Substituted 4-cyano-3-phenyl-4-(pyridin-3-yl)butanoates, processes for preparation thereof and use thereof as herbicides and plant growth regulators

ABSTRACT

Compounds of the formula (I) or salts thereof, 
                         
in which (R 1 ) m , (R 2 ) n , R 3  and R 4  as defined in Claim  1  are suitable as herbicides for the control of harmful plants or as plant growth regulators.
 
     The compounds can be prepared by the processes of Claim  7.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a §371 National Stage Application ofPCT/EP2012/071391, filed Oct. 29, 2012, which claims priority to EP11187228.9, filed Oct. 31, 2011.

BACKGROUND

1. Field of the Invention

The invention relates to the technical field of the herbicides and plantgrowth regulators, preferably the herbicides for controlling unwantedvegetation or the herbicides for the selective control of broad-leavedweeds and weed grasses in crops of useful plants, or the plant growthregulators which can be used for influencing the growth of crop plants.

2. Description of Related Art

In their application, crop protection agents known to date for theselective control of harmful plants in crops of useful plants or activecompounds for controlling unwanted vegetation sometimes havedisadvantages, be it (a) that they have no or else insufficientherbicidal activity against particular harmful plants, (b) that thespectrum of harmful plants which can be controlled with an activecompound is not wide enough, (c) that their selectivity in crops ofuseful plants is too low and/or (d) that they have a toxicologicallyunfavorable profile. Furthermore, some active compounds which can beused as plant growth regulators for a number of useful plants causeunwanted reduced harvest yields in other useful plants or are notcompatible with the crop plant, or only within a narrow application raterange. Some of the known active compounds cannot be producedeconomically on an industrial scale owing to precursors and reagentswhich are difficult to obtain, or they have only insufficient chemicalstabilities. In the case of other active compounds, the activity is toohighly dependent on environmental conditions, such as weather and soilconditions.

The published patent applications EP-A-5341, EP-A-266725, EP-A-270830,JP-04/297454, JP-04/297455, JP-05/058979, WO 2011/003775, WO2011/003776, WO 2011/042378, WO 2011/073143 and WO2011/098417 discloseherbicidal cyanobutyrates.

EP-A-5341 describes herbicidal esters and amides of4-cyano-3,4-diarylbutanoic acids. The aryl radicals mentioned areoptionally substituted phenyl radicals and unsubstituted pyridyl orthienyl. The specific examples include mainly4-cyano-3,4-diphenylbutanoic acids and esters. There are two specificexamples of compounds containing pyridyl, namely4-cyano-4-phenyl-4-(pyridin-3-yl)butanoic acid and the correspondingethyl ester.

According to EP-A-5341, the threo isomers are generally suitable for thenon-selective control of harmful plants, whereas the erythro/threoisomer mixtures are suitable for the selective control of harmful plantsin some crops of useful plants. Moreover, EP-A-5341 mentions that the 2enantiomers belonging to the threo form differ in their activities,which was studied in an exemplary manner using the different activitiesof the enantiomers of the enantiomer pair of4-cyano-3,4-diphenylbutanoic acid having unsubstituted phenyl radicals.

EP-A-266725 discloses a number of erythro/threo isomer mixtures of4-cyano-3,4-diphenylbutanoic acids and derivatives thereof which can beused for the selective control of weeds in rice crops.

EP-A-270830 describes that threo isomers and erythro/threo isomermixtures of 4-cyano-3,4-diarylbutanoic acid (esters) can be used asplant regulators, preventing the development of an infructescence invarious harmful grasses. The aryl radicals mentioned are optionallysubstituted phenyl radicals and unsubstituted pyridyl orhalogen-substituted pyridyl. Specific examples relate mainly to(substituted) 4-cyano-3,4-diphenylbutanoic acid (esters). Additionallydescribed are also 4-cyano-3-pyridyl-4-phenylbutanoic acid esters, suchas the compound ethyl 4-cyano-3-pyridyl-4-phenylbutanoate, or4-cyano-3-phenyl-4-pyridylbutanoic acid ester, such as the compoundmethyl 4-cyano-3-(4-chlorophenyl)-4-(6-fluoropyridin-3-yl)butanoate.JP-04/297455 discloses herbicidal 4-cyano-3-phenyl-4-heteroarylbutanoicacid (esters), where the heterocyclic radicals are selected from thegroup consisting of 1,2,4-triazolyl, 1-pyrazolyl, 1-imidazolyl, 2- and3-thienyl, 2- and 3-pyridyl, 1-methylpyrrol-2-yl, 2-quinolinyl,2-methyl-3-trifluoromethylpyrazol-5-yl and5-trifluoromethylpyridin-2-yl. Specific compounds from the 3-pyridylseries only comprise unsubstituted pyridin-3-yl radicals, for examplethe compounds propargyl and allyl4-cyano-3-phenyl-4-(pyridin-3-yl)butanoate.

WO 2011/003775 discloses specific esters of 4-cyano-3,4-diphenylbutanoicacids which can be used as effective herbicides, preferably also incrops of useful plants. WO 2011/003776, WO 2011/042378, WO 2011/073143and WO2011/098417 disclose 4-cyano-3,4-diphenylbutanoic acids and esterswhich have specific substitutions at the phenyl radicals and can be usedas effective herbicides, preferably also in crops of useful plants.

The herbicidal activity of the known compounds of the class ofsubstances mentioned, in particular at low application rates, and/ortheir compatibility with crop plants, remain deserving of improvement.

For the reasons mentioned, there is still a need for alternative, highlyactive herbicides for the selective application in plant crops or use onnon-crop land. It is also desirable to provide alternative chemicalactive compounds which may be used in an advantageous manner asherbicides or plant growth regulators.

Likewise desirable are compounds having herbicidal activity which arehighly effective against economically important harmful plants even atrelatively low application rates and can be used selectively in cropplants, preferably with good activity against harmful plants.

SUMMARY

Surprisingly it has now been found that certain heterocyclicallysubstituted cyanobutyrates have particular herbicidal activities and canpreferably be employed in some crops selectively for controlling harmfulplants.

The present invention provides compounds of the formula (I) or saltsthereof

in which

-   (R¹)_(m) represents m substituents R¹,    -   where R¹, if m=1, or each of the substituents R¹, if m is        greater than 1, independently of the others represents halogen,        cyano, nitro, hydroxy, (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio,        (C₁-C₈)-alkylsulphinyl, (C₁-C₈)-alkylsulphonyl,        (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio,        (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl,        (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,        (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl,        (C₃-C₆)-cycloalkyl which is optionally substituted by one or        more radicals from the group consisting of halogen and        (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally        substituted by one or more radicals from the group consisting of        halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR⁵,        C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ or Het²    -   or where in each case two groups R¹ located ortho at the ring or        R¹ and R³ together represent a group of the formula —Z¹-A*-Z² in        which    -   A* represents an alkylene group having 1 to 4 carbon atoms which        is optionally substituted by one or more radicals from the group        consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,    -   Z¹ represents a direct bond, O or S and    -   Z² represents a direct bond, O or S,    -   where the group —Z¹-A*-Z² together with the carbon atoms,        attached to the group, of the phenyl ring form a fused-on 5- or        6-membered ring,-   (R²)_(n) represents n substituents R²,    -   where R², if n=1, or each of the substituents R², if n is        greater than 1, independently of the others represents halogen,        cyano, nitro, hydroxy, (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio,        (C₁-C₈)-alkylsulphinyl, (C₁-C₈)-alkylsulphonyl,        (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio,        (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl,        (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,        (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl,        (C₃-C₆)-cycloalkyl which is optionally substituted by one or        more radicals from the group consisting of halogen and        (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally        substituted by one or more radicals from the group consisting of        halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR¹⁰,        C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ or Het⁴    -   or where in each case two groups R² located ortho at the ring        together are a group of the formula —Z³-A**-Z⁴ in which    -   A** represents an alkylene group having 1 to 4 carbon atoms        which is optionally substituted by one or more radicals from the        group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,    -   Z³ represents a direct bond, O or S and    -   Z⁴ represents a direct bond, O or S,    -   where the group —Z³-A**-Z⁴ together with the carbon atoms,        attached to the group, of the phenyl ring form a fused-on 5- or        6-membered ring,-   R³ represents halogen, cyano, nitro, hydroxy, (C₁-C₈)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio,    (C₁-C₈)-alkylsulphinyl, (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkyl,    (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio,    (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl,    (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,    (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkyl which is optionally substituted by one or more    radicals from the group consisting of halogen and (C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more    radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or    a radical of the formula C(O)OR¹⁵, C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹    or Het⁶,-   R⁴ represents hydrogen or a hydrolyzable radical, preferably    -   R⁴ represents hydrogen or an optionally substituted hydrocarbon        radical or an optionally substituted heterocyclyl radical, where        each of the two last-mentioned carbon-containing radicals        including substituents has 1 to 30 carbon atoms, preferably 1 to        24 carbon atoms, in particular 1 to 20 carbon atoms, or    -   R⁴ represents a radical of the formula SiR^(a)R^(b)R^(c),        —NR^(a)R^(b) or —N═CR^(c)R^(d), where in the 3 last-mentioned        formulae each of the radicals R^(a), R^(b), R^(c) and R^(d)        independently of the others represents hydrogen or an optionally        substituted hydrocarbon radical, where, however, SiH₃ for        SiR^(a)R^(b)R^(c) is excluded, or R^(a) and R^(b) together with        the nitrogen atom of the group —NR^(a)R^(b) represent a 3- to        9-membered heterocycle which, in addition to the nitrogen atom,        may contain one or two further ring heteroatoms from the group        consisting of N, O and S and which is unsubstituted or        substituted, or R^(c) and R^(d) together with the carbon atom of        the group —N═CR^(c)R^(d) represent a 3- to 9-membered        carbocyclic radical or a heterocyclic radical which may contain        1 to 3 ring heteroatoms from the group consisting of N, O and S,        where the carbocyclic or heterocyclic radical is unsubstituted        or substituted,        -   where each of the radicals R^(a), R^(b), R^(c) and R^(d)            including substituents has up to 30 carbon atoms, preferably            up to 24 carbon atoms, in particular up to 20 carbon atoms,            or    -   R⁴ represents a radical of the formula —C(═O)—R^(e) or        —P(═O)(R^(f))₂, where R^(e) and the radicals R^(f) independently        of one another each represent hydrogen, OH, (C₁-C₈)-alkyl,        (C₁-C₄)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,        (C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₈)-alkyl,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkoxy-(C₁-C₈)-alkyl,        (C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₈)-alkyl,        (C₃-C₈)-alkynyloxy, (C₃-C₈)-alkynyloxy-(C₁-C₈)-alkyl, —NR*R**,        with R* and R** being defined below, tri-[(C₁-C₄)-alkyl]silyl,        tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₈)alkyl, (C₃-C₆)-cycloalkyl,        (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkenyl,        (C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkynyl,        (C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkyl, phenyl,        phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl,        phenylamino, phenylamino-(C₁-C₈)-alkyl, a radical Het⁷,        Het⁷-(C₁-C₆)-alkyl or Het⁷-O—(C₁-C₆)-alkyl,        -   where each of the 15 last-mentioned radicals is            unsubstituted in the acyclic moiety or substituted by one or            more identical or different radicals R^(A) and is            unsubstituted in the cyclic moiety or substituted by one or            more identical or different radicals R^(B),-   R⁵, R¹⁰ and R¹⁵ independently of one another each represent    hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-alkynyl or the group M mentioned below, preferably    (C₁-C₄)-alkyl,-   R⁶, R⁷, R⁸, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁶, R¹⁷, R¹⁸ and R¹⁹    independently of one another each represent hydrogen, (C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, where each of the 3    last-mentioned radicals independently of the others is unsubstituted    or substituted by one or more radicals from the group consisting of    halogen, nitro, cyano and phenyl which is optionally substituted,    preferably unsubstituted or substituted by one or more radicals from    the group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl and    (C₁-C₄)-haloalkyl, or (C₃-C₆)-cycloalkyl or phenyl, where each of    the 2 last-mentioned radicals in each case independently of the    other is unsubstituted or substituted by one or more radicals from    the group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, phenyl and benzyl, where each of the 2    last-mentioned radicals is optionally substituted, preferably    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl and    (C₁-C₄)-haloalkyl,-   Het¹, Het², Het³, Het⁴, Het⁵ and Het⁶ independently of one another    each represent a saturated or partially unsaturated radical of a    heterocycle having 3 to 9 ring atoms and at least one nitrogen atom    as ring heteroatom at position 1 of the ring and optionally 1, 2 or    3 further ring heteroatoms from the group consisting of N, O and S,    where the radical of the heterocycle at the nitrogen atom in    position 1 of the ring is attached to the remainder of the molecule    of the compound of the formula (I) and where the heterocycle is    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo,    preferably the radical of a saturated heterocycle of the type    mentioned, in particular a morpholino, piperidino or pyrrolidino    group,-   Het⁷ independently of the others in each case represents a    saturated, partially unsaturated or heteroaromatic monocyclic    heterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-membered    bicyclic heterocycle, each containing 1, 2, 3 or 4 heteroatoms    selected from the group consisting of O, N and S,-   R*, R** independently of one another (and also independently of    other radicals NR*R**) each represent H, (C₁-C₈-alkyl,    (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₆)-alkanoyl, [(C₁-C₄)-haloalkyl]carbonyl,    [(C₁-C₄)-alkoxy]carbonyl, [(C₁-C₄)-haloalkoxy]carbonyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl,    phenyl-(C₁-C₄)-alkyl, where each of the 4 last-mentioned radicals is    optionally substituted in the cycle by one or more identical or    different radicals from the group consisting of halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and    (C₁-C₄)-haloalkoxy or, in the case of saturated or partially    unsaturated cyclic base groups, also oxo, or-   R* and R** together with the nitrogen atom represent a 3- to    8-membered heterocycle which, in addition to the nitrogen atom, may    contain one or two further ring heteroatoms from the group    consisting of N, O and S and which may be unsubstituted or    substituted by one or more radicals from the group consisting of    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,-   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy,-   R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₈)-alkyl,    (C₁-C₆)-haloalkyl, cyano-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkyl,    nitro-(C₁-C₆)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl,    (C₂-C₈)-alkynyl, (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy,    (C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkoxy,    (C₁-C₈)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,    (C₁-C₈)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,    (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of the    formula R^(aa)—C(═O)—, R^(aa)—C(═O)—(C₁-C₆)alkyl, the radicals    R^(aa) being defined below, —NR*R**, R* and R** being defined below,    tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,    (C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkoxy,    (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy,    phenyl, phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl,    phenylamino, phenylamino-(C₁-C₈)-alkyl or a 5- or 6-membered    monocyclic or 9- or 10-membered bicyclic heterocycle which contains    1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N    and S, where each of the 11 last-mentioned radicals is optionally    substituted in the cyclic moiety by one or more identical or    different radicals R^(bb),-   R^(aa) independently of one another each represent hydrogen, OH,    (C₁-C₈)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,    (C₁-C₈)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy, (C₁-C₆)-haloalkoxy,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkoxy,    (C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkyl,    (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkoxy, (C₃-C₈)-alkynyloxy,    (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkyl, (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkoxy,    —NR*R*, where R* and R** are as defined above,    tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkyl,    tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl,    (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, (C₅-C₈)-cycloalkenyl,    (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₈)-cycloalkenyloxy,    (C₅-C₈)-cycloalkynyl, (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl,    (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl,    phenyl-(C₁-C₈)-alkoxy, phenoxy, phenoxy-(C₁-C₈)-alkyl,    phenoxy-(C₁-C₈)-alkoxy, phenylamino, phenylamino-(C₁-C₈)-alkyl,    phenylamino-(C₁-C₈)-alkoxy or a 5- or 6-membered monocyclic or 9- or    10-membered bicyclic heterocycle which is optionally attached via an    alkylene group or an alkoxy group and contains 1, 2, 3 or 4    heteroatoms selected from the group consisting of O, N and S, where    each of the 20 last-mentioned radicals is optionally substituted in    the cyclic moiety by one or more identical or different radicals    R^(cc), and-   R^(bb) and R^(cc) independently of one another each represent    halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or    (C₁-C₄)-haloalkoxy or in the case of saturated or partially    unsaturated cyclic base groups also represent oxo and-   M represents an equivalent of a cation,    -   preferably a metal ion equivalent, an ammonium ion which is        optionally substituted by 1 to 4 identical or different radicals        from the group consisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl,        (C₅-C₆)-cycloalkynyl, phenyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,        (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl, or a        tertiary sulphonium ion which is preferably substituted by 3        identical or different radicals from the group consisting of        (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,        (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl,        phenyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,        (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl, in        particular (C₁-C₄)-alkyl,-   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or    1, and-   n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

In the formula (I), the formula “(R¹)_(m)” means m radicals R¹ which areattached as substituents at the pyridyl ring in question, where theradicals in the case of m greater than 1 may be identical or differentand have the meaning mentioned in each case in more detail. In the casem=0, the pyridyl ring in question is not substituted by substituents R¹,i.e. all ring carbon atoms of the pyridyl ring in positions 2, 4 and 6of the pyridin-3-yl radical are attached to a hydrogen atom.

In the formula (I), the formula “(R²)_(n)” means n radicals R² which areattached as substituents at the phenyl ring in question, where theradicals in the case of n greater than 1 may be identical or differentand have the meaning mentioned in each case in more detail. In the casen=0, the phenyl ring in question is not substituted by substituents R²,i.e. all ring carbon atoms of the phenyl ring in positions 2 to 6 of thephenyl radical are attached to a hydrogen atom.

The compounds of the formula (I) according to the invention include allstereoisomers which can occur on the basis of the centres of asymmetryor double bonds in the molecule whose configuration is not designatedspecifically in the formula or which are not specified explicitly, andmixtures thereof, including the racemic compounds and the mixturesenriched partly with particular stereoisomers. The invention alsoincludes all tautomers, such as keto and enol tautomers, and theirmixtures and salts, if appropriate functional groups are present.

In positions 3 and 4 of the substituted butanoic acid skeleton, thecompounds of the formula (I) contain two centres of chirality, and theytherefore occur as at least four stereoisomers and mixtures thereof,i.e. 2 enantiomeric erythro isomers and 2 enantiomeric threo isomers.Depending on the substituents (R¹)_(m) and (R²)_(n) R³ and R⁴, one ormore further centres of chirality may be present.

Accordingly, the invention also provides erythro/threo mixtures(diastereomer mixtures) of the compounds of the formula (I).

The invention also provides the racemic erythro isomers or the racemicthreo isomers of the compounds of the formula (I).

The invention also provides the optically active (3R, 4S) and (3S, 4R)erythro isomers and mixtures thereof having an excess of one enantiomer.

The invention also provides the optically active (3R, 4R) and (3S, 4S)threo isomers and mixtures thereof having an excess of one enantiomer.

Owing to the two centres of chirality in positions 3 and 4, compounds ofthe same chemical constitution exist as 4 stereoisomeric configurations,namely two erythro enantiomers having the configurations (3S,4R)[=erythro-1] and (3R,4S) [=erythro-2], respectively, and two threoenantiomers having the configurations (3S,4S) [=threo-1] and (3R,4R)[=threo-2], respectively; see the scheme below:

The compounds (I) according to the invention represent diastereomermixtures of the 4 stereoisomers, but also embrace the separateddiastereomeric erythro or threo forms, in each case as a racemic mixtureof the erythro enantiomers or threo enantiomers or as pure orstereochemically enriched enantiomers erythro-1, erythro-2, threo-1 orthreo-2 mentioned above.

Preference is given to the diastereomer mixtures of the formula (I)(erythro/threo mixtures).

Preference is also given to the racemic erythro mixtures of the formula(I) of the aforementioned enantiomers erythro-1 and erythro-2 in a ratioof 50:50.

Preference is furthermore given to the racemic threo mixtures of theformula (I) of the aforementioned enantiomers threo-1 and threo-2 in aratio of 50:50.

More preference is given to the (3R,4R) enantiomers threo-2 of theformula (Ia) or salts thereof

in which (R¹)_(m) and (R²)_(n) are as defined in formula (I),where the stereochemical configuration at the carbon atom in position 3of the butanoic acid derivative has a stereochemical purity of 60 to100% (R), preferably 70 to 100% (R), more preferably 80 to 100% (R), inparticular 90 to 100% (R), based on the mixture of threo enantiomerspresent, andthe stereochemical configuration at the carbon atom in position 4 of thebutanoic acid derivative has a stereochemical purity of 60 to 100% (R),preferably 70 to 100% (R), more preferably 80 to 100% (R), in particular90 to 100% (R), based on the mixture of threo enantiomers present.

In the case of R⁴═H or in the case of suitable acidic substituents, thecompounds of the formula (I) are able to form salts by reaction withbases where the acidic hydrogen is replaced by an agriculturallysuitable cation.

By addition of a suitable inorganic or organic acid onto a basic group,such as, for example, amino or alkylamino or else the nitrogen atom inthe pyridyl ring, the compounds of the formula (I) are able to formsalts. Suitable acidic groups present, such as, for example, carboxylicacid groups, are able to form inner salts with groups which for theirpart can be protonated, such as amino groups.

The compounds of the formula (I) may preferably be present in the formof agriculturally usable salts, where the type of salt is generallyotherwise immaterial. In general, suitable salts are the salts of thosecations or the acid addition salts of those acids whose cations andanions, respectively, have no adverse effect on the herbicidal activityof the compounds (I).

Suitable cations are in particular the ions of the alkali metals,preferably lithium, sodium or potassium, of the alkaline earth metals,preferably calcium or magnesium, and of the transition metals,preferably manganese, copper, zinc or iron. The cation used may also beammonium or substituted ammonium, where one to four hydrogen atoms maybe replaced here by (C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,phenyl or benzyl, preferably ammonium, dimethylammonium,diisopropylammonium, tetramethylammonium, tetrabutylammonium,2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium,trimethylbenzylammonium. Also suitable are phosphonium ions, sulphoniumions, preferably tri(C₁-C₄)sulphonium, in particulartrimethylsulphonium, or sulphoxonium ions, preferablytri(C₁-C₄)sulphoxonium, in particular trimethylsulphoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogensulphate, sulphate, dihydrogenphosphate,hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and also the anions of (C₁-C₄)-alkanoicacids, preferably formate, acetate, propionate, butyrate ortrifluoroacetate.

In formula (I) and in all subsequent formulae, chemical radicals arereferred to by names which are collective terms for the enumeration ofindividual group members or specifically refer to individual chemicalradicals. In general, terms are used which are familiar to the personskilled in the art and/or in particular have the meanings illustratedbelow.

A hydrolyzable radical (see definition of R⁴) is a radical which can behydrolyzed under application conditions, for example a radical which canbe hydrolyzed even in the spray liquor or in particular under thephysiological conditions in plants, where a compound of the formula (I)having the carboxylic ester group —CO—OR⁴ (R⁴ is not hydrogen) ishydrolyzed to the compound of the formula (I) having the carboxylic acidgroup —CO—OH (i.e. the compound (I) where R⁴═H). Expressly, thedefinition of the hydrolyzable radicals also includes radicals whereR⁴=hydrocarbon radical or heterocyclyl radical, the two last-mentionedradicals being unsubstituted or substituted, even if some of them arehydrolyzable comparatively slowly.

A hydrocarbon radical is an aliphatic, cycloaliphatic or aromaticmonocyclic or, in the case of an optionally substituted hydrocarbonradical, also a bicyclic or polycyclic organic radical based on theelements carbon and hydrogen, including, for example, the radicalsalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl,naphthyl, indanyl, indenyl, etc.; this applies correspondingly tohydrocarbon radicals in composite meanings, such as hydrocarbonoxyradicals or other hydrocarbon radicals attached via heteroatom groups.

Unless defined in more detail, the hydrocarbon radicals preferably have1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, inparticular 1 to 12 carbon atoms. The hydrocarbon radicals, also in thespecial radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino andalkylthio, and also the corresponding unsaturated and/or substitutedradicals may in each case be straight-chain or branched in the carbonskeleton.

The expression “(C₁-C₄)-alkyl” is a brief notation for alkyl having from1 to 4 carbon atoms, i.e. encompasses the methyl, ethyl, 1-propyl,2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radicals.General alkyl radicals with a larger specified range of carbon atoms,e.g. “(C₁-C₆)-alkyl”, correspondingly also encompass straight-chain orbranched alkyl radicals with a greater number of carbon atoms, i.e.according to the example also the alkyl radicals having 5 and 6 carbonatoms.

Unless stated specifically, preference is given to the lower carbonskeletons, for example having from 1 to 6 carbon atoms, or having from 2to 6 carbon atoms in the case of unsaturated groups, in the case of thehydrocarbyl radicals such as alkyl, alkenyl and alkynyl radicals,including in composite radicals. Alkyl radicals, including in thecombined definitions such as alkoxy, haloalkyl, etc., are, for example,methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexylssuch as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such asn-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynylradicals are defined as the possible unsaturated radicals correspondingto the alkyl radicals; alkenyl is, for example, vinyl, allyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl,2-methylpentenyl or hexenyl group, preferably allyl,1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,but-3-en-1-yl, 1-methylbut-3-en-1-yl or 1-methylbut-2-en-1-yl.

Alkenyl also includes in particular straight-chain or branchedhydrocarbon radicals having more than one double bond, such as1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenylradicals having one or more cumulated double bonds, for example allenyl(1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.

Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,1-methylbut-3-yn-1-yl. Alkynyl also includes, in particular,straight-chain or branched hydrocarbon radicals having more than onetriple bond or else having one or more triple bonds and one or moredouble bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1-yl.

A 3- to 9-membered carbocyclic ring is (C₃-C₉)-cycloalkyl or(C₅-C₉)-cycloalkenyl. (C₃-C₉)-Cycloalkyl is a carbocyclic saturated ringsystem having preferably 3-9 carbon atoms, for example cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl orcyclononyl. In the case of substituted cycloalkyl, cyclic systems withsubstituents are included, where the substituents may also be bonded bya double bond on the cycloalkyl radical, for example an alkylidene groupsuch as methylidene. (C₅-C₉)-Cycloalkenyl is a carbocyclic, nonaromatic,partially unsaturated ring system having 5-9 carbon atoms, for example1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl,3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl,1,3-cyclohexadienyl or 1,4-cyclohexadienyl. In the case of substitutedcycloalkenyl, the explanations for substituted cycloalkyl applycorrespondingly.

Alkylidene, for example also in the form of (C₁-C₁₀)-alkylidene, is theradical of a straight-chain or branched alkane which is bonded via adouble bond, the position of the binding site not being fixed. In thecase of a branched alkane, the only positions possible are, of course,those in which two hydrogen atoms can be replaced by the double bond;radicals are, for example, ═CH₂, ═CH—CH₃, ═C(CH₃)—CH₃, ═C(CH₃)—C₂H₅ or═C(C₂H₅)—C₂H₅.

Halogen is, for example, fluorine, chlorine, bromine or iodine.Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl and alkynyl,respectively, which are partially or fully substituted by identical ordifferent halogen atoms, preferably from the group consisting offluorine, chlorine, bromine and iodine, in particular from the groupconsisting of fluorine, chlorine and bromine, very particularly from thegroup consisting of fluorine and chlorine, for example monohaloalkyl,perhaloalkyl, CF₃, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl, CCl₃, CHCl₂, CH₂CH₂Cl;haloalkoxy is, for example, OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ andOCH₂CH₂Cl; this applies correspondingly to haloalkenyl and otherhalogen-substituted radicals such as, for example, halocycloalkyl.

Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl,naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyland the like, preferably phenyl.

Optionally substituted aryl also includes polycyclic systems, such astetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where thepoint of attachment is at the aromatic system.

A heterocyclic radical (heterocyclyl) comprises at least oneheterocyclic ring (=carbocyclic ring in which at least one carbon atomis replaced by a heteroatom, preferably by a heteroatom from the groupconsisting of N, O, S, P, B, Si, Se), which is saturated, unsaturated orheteroaromatic and may be unsubstituted or substituted, where the pointof attachment is located at a ring atom.

Unless defined otherwise it preferably contains one or more, inparticular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferablyfrom the group consisting of N, O, and S; it is preferably an aliphaticheterocyclyl radical having 3 to 7 ring atoms or a heteroaromaticradical having 5 or 6 ring atoms. The heterocyclic radical may, forexample, be a heteroaromatic radical or ring (heteroaryl), such as, forexample, a monocyclic, bicyclic or polycyclic aromatic system in whichat least 1 ring contains one or more heteroatoms.

If the heterocyclyl radical or the heterocyclic ring is optionallysubstituted, it can be fused to other carbocyclic or heterocyclic rings.Preference is given to benzo-fused heterocyclic or heteroaromatic rings.

Optionally substituted heterocyclyl also includes polycyclic systems,such as, for example, 8-aza-bicyclo[3.2.1]octanyl or1-aza-bicyclo[2.2.1]heptyl.

Optionally substituted heterocyclyl also includes spirocyclic systems,such as, for example, 1-oxa-5-aza-spiro[2.3]hexyl.

It is preferably a radical of a heteroaromatic ring having a heteroatomfrom the group consisting of N, O and S, for example the radical of afive- or six-membered ring, such as pyridyl, pyrrolyl, thienyl or furyl;

it is furthermore preferably a radical of a corresponding heteroaromaticring having 2, 3 or 4 heteroatoms, for example pyrimidinyl, pyridazinyl,pyrazinyl, triazinyl, tetrazinyl, thiazolyl, thiadiazolyl, oxazolyl,isoxazolyl, pyrazolyl, imidazolyl or triazolyl or tetrazolyl. Here,preference is given to a radical of a heteroaromatic five- orsix-membered ring having 1 to 4 heteroatoms, such as, for example,1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, 1,2,3-triazinyl,1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3,4-tetrazinyl,1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, thiazolyl, isothiazolyl,oxazolyl, isoxazolyl, pyrazolyl, imidazolyl.

More preference is given here to heteroaromatic radicals offive-membered heterocycles having 3 nitrogen atoms, such as1,2,3-triazol-1-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl,1,2,5-triazol-1-yl, 1,2,5-triazol-3-yl, 1,3,4-triazol-1-yl,1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl;

more preference is also given here to heteroaromatic radicals ofsix-membered heterocycles having 3 nitrogen atoms, such as1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl;

more preference is also given here to heteroaromatic radicals offive-membered heterocycles

having two nitrogen atoms and one oxygen atom, such as1,2,4-oxadiazol-3-yl; 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl,1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl,

more preference is also given here to heteroaromatic radicals offive-membered heterocycles having two nitrogen atoms and one sulphuratom, such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl,1,2,5-thiadiazol-3-yl;more preference is also given here to heteroaromatic radicals offive-membered heterocycles having four nitrogen atoms, such as1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-5-yl, 1,2,3,5-tetrazol-1-yl,1,2,3,5-tetrazol-4-yl, 2H-1,2,3,4-tetrazol-5-yl,1H-1,2,3,4-tetrazol-5-yl,more preference is also given here to heteroaromatic radicals ofsix-membered heterocycles such as 1,2,4,5-tetrazin-3-yl;more preference is also given here to heteroaromatic radicals offive-membered heterocycles having three nitrogen atoms and one oxygen orsulphur atom, such as 1,2,3,4-oxatriazol-5-yl; 1,2,3,5-oxatriazol-4-yl;1,2,3,4-thiatriazol-5-yl; 1,2,3,5-thiatriazol-4-yl;more preference is also given here to heteroaromatic radicals ofsix-membered heterocycles such as, for example,1,2,4,6-thiatriazin-1-yl; 1,2,4,6-thiatriazin-3-yl;1,2,4,6-thiatriazin-5-yl.

Furthermore preferably, the heterocyclic radical or ring is a partiallyor fully hydrogenated heterocyclic radical having one heteroatom fromthe group consisting of N, O and S, for example oxiranyl, oxetanyl,oxolanyl (=tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl orpiperidyl.

It is also preferably a partially or fully hydrogenated heterocyclicradical having 2 heteroatoms from the group consisting of N, O and S,for example piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl,oxazolidinyl, isoxazolidinyl and morpholinyl. Suitable substituents fora substituted heterocyclic radical are the substituents specified lateron below, and additionally also oxo. The oxo group may also occur on thehetero-ring atoms which are able to exist in different oxidation states,as in the case of N and S, for example.

Preferred examples of heterocyclyl are a heterocyclic radical havingfrom 3 to 6 ring atoms from the group consisting of pyridyl, thienyl,furyl, pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl(=tetrahydrofuryl), pyrrolidyl, piperidyl, especially oxiranyl,2-oxetanyl, 3-oxetanyl or oxolanyl, or is a heterocyclic radical havingtwo or three heteroatoms, for example pyrimidinyl, pyridazinyl,pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl,pyrazolyl, triazolyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl,oxazolidinyl, isoxazolidinyl or morpholinyl.

Preferred heterocyclic radicals are also benzo-fused heteroaromaticrings, for example benzofuryl, benzisofuryl, benzothiophenyl,benzisothiophenyl, isobenzothiophenyl, indolyl, isoindolyl, indazolyl,benzimidazolyl, benzotriazolyl, benzoxazolyl, 1,2-benzisoxazolyl,2,1-benzisoxazolyl, benzothiazolyl, 1,2-benzisothiazolyl,2,1-benzisothiazolyl, 1,2,3-benzoxadiazolyl, 2,1,3-benzoxadiazolyl,1,2,3-benzothiadiazolyl, 2,1,3-benzothiadiazolyl, quinolyl (quinolinyl),isoquinolyl (isoquinolinyl), quinnolinyl, phthalazinyl, quinazolinyl,quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl,indolizinyl, benzo-1,3-dioxylyl, 4H-benzo-1,3-dioxinyl and4H-benzo-1,4-dioxinyl, and, where possible, N-oxides and salts thereof.

When a base structure is substituted “by one or more radicals” from alist of radicals (=group) or a generically defined group of radicals,this in each case includes simultaneous substitution by a plurality ofidentical and/or structurally different radicals. Substituted radicals,such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, phenyl,benzyl, heterocyclyl and heteroaryl radical, are, for example, asubstituted radical derived from the unsubstituted base structure, wherethe substituents are, for example, one or more, preferably 1, 2 or 3,radicals from the group consisting of halogen, alkoxy, alkylthio,hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl,alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl,substituted amino such as acylamino, mono- and dialkylamino, andalkylsulphinyl, alkylsulphonyl and, in the case of cyclic radicals, alsoalkyl, haloalkyl, alkylthioalkyl, alkoxyalkyl, optionally substitutedmono- and dialkylaminoalkyl and hydroxyalkyl; in the term “substitutedradicals”, such as substituted alkyl, etc., substituents include, inaddition to the saturated hydrocarbon radicals mentioned, correspondingunsaturated aliphatic and aromatic radicals, such as optionallysubstituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl andphenoxy. In the case of substituted cyclic radicals having aliphaticmoieties in the ring, cyclic systems with those substituents which arebonded on the ring by a double bond are also included, for examplesubstituted by an alkylidene group such as methylidene or ethylidene.

The term “radicals from the group consisting of (followed by thegroup=list of the substituents)” is, wherever used, meant to besynonymous with “radicals selected from the group consisting of ( . . .)”. The term “one or more radicals from the group consisting of(followed by the group=list of the substituents)” is, wherever used,meant to be synonymous with “one or more identical or different radicalsselected from the group consisting of ( . . . )”.

The substituents given by way of example (“first substituent level”)can, if they include hydrocarbon-containing fractions, be furthersubstituted therein if desired (“second substituent level”), by forexample one of the substituents as defined for the first substituentlevel. Corresponding further substituent levels are possible. The term“substituted radical” preferably embraces just one or two substituentlevels.

“Parent radical” refers to the respective base structure of a radical towhich substituents of a substituent level are attached.

Preferred substituents for the substituent levels are, for example,amino, hydroxyl, halogen, nitro, cyano, mercapto, carboxyl, carbonamide,SF₅, aminosulphonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl,monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy,alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl,alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio,cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio,alkylsulphinyl, alkylsulphonyl, monoalkylaminosulphonyl,dialkylaminosulphonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl,N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylaminocarbonyl, aryl, aryloxy,benzyl, benzyloxy, benzylthio, arylthio, arylamino and benzylamino. Twosubstituents together may also form a saturated or unsaturatedhydrocarbon bridge or a corresponding bridge in which carbon atoms, CHgroups or CH₂ groups are replaced by heteroatoms, thus forming afused-on or fused cycle. Here, with preference benzo-fused systems basedon the base structure are formed.

Optionally substituted phenyl is preferably phenyl or phenyl which isunsubstituted or substituted by one or more radicals from the groupconsisting of halogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy-(C₁-C₄)alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio and nitro, inparticular phenyl which is optionally substituted by one or moreradicals from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl and (C₁-C₄)-alkoxy.

In the case of radicals having carbon atoms, preference is given tothose having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms,especially 1 or 2 carbon atoms. Preference is generally given tosubstituents from the group consisting of halogen, e.g. fluorine andchlorine, (C₁-C₄)-alkyl, preferably methyl or ethyl, (C₁-C₄)-haloalkyl,preferably trifluoromethyl, (C₁-C₄)-alkoxy, preferably methoxy orethoxy, (C₁-C₄)-haloalkoxy, nitro and cyano. Particular preference isgiven here to the substituents methyl, methoxy, fluorine and chlorine.

Substituted amino, such as mono- or disubstituted amino, is a radicalfrom the group consisting of the substituted amino radicals which areN-substituted, for example, by one or two identical or differentradicals from the group consisting of alkyl, alkoxy, acyl and aryl;preferably mono- and dialkylamino, mono- and diarylamino, acylamino,N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; preferenceis given to alkyl radicals having from 1 to 4 carbon atoms; aryl ispreferably phenyl or substituted phenyl; acyl is as defined below,preferably (C₁-C₄)-alkanoyl. The same applies to substitutedhydroxylamino or hydrazino.

Acyl is a radical of an organic acid which arises in a formal sense byremoval of a hydroxyl group on the acid function, and the organicradical in the acid may also be bonded to the acid function via aheteroatom. Examples of acyl are the —CO—R radical of a carboxylic acidHO—CO—R and radicals of acids derived therefrom, such as those ofthiocarboxylic acid, optionally N-substituted iminocarboxylic acids orthe radical of carbonic monoesters, N-substituted carbamic acid,sulphonic acids, sulphinic acids, N-substituted sulphonamide acids,phosphonic acids or phosphinic acids.

Acyl is, for example, formyl, alkylcarbonyl such as[(C₁-C₄)-alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl,phenyloxycarbonyl, benzyloxycarbonyl, alkylsulphonyl, alkylsulphinyl,N-alkyl-1-iminoalkyl and other radicals of organic acids. The radicalsmay each be substituted further in the alkyl or phenyl moiety, forexample in the alkyl moiety by one or more radicals from the groupconsisting of halogen, alkoxy, phenyl and phenoxy; examples ofsubstituents in the phenyl moiety are the substituents already mentionedabove in general for substituted phenyl.

Acyl is preferably an acyl radical in the narrower sense, i.e. a radicalof an organic acid in which the acid group is bonded directly to thecarbon atom of an organic radical, for example formyl, alkylcarbonylsuch as acetyl or [(C₁-C₄)-alkyl]carbonyl, phenylcarbonyl,alkylsulphonyl, alkylsulphinyl and other radicals of organic acids.

More preferably, acyl is an alkanoyl radical having 1 to 6 carbon atoms,in particular 1 to 4 carbon atoms. Here, (C₁-C₄)-alkanoyl is the radicalof an alkanoic acid having 1 to 4 carbon atoms formed after removal ofthe OH group of the acid group, i.e. formyl, acetyl, n-propionyl,isopropionyl or n-, i-, sec- or tert-butanoyl.

The “yl position” of a radical denotes the carbon atom having the freebond.

Compounds of the formula (I) according to the invention and compounds ofthe formula (I) used according to the invention and/or salts thereof arein short also referred to as “compounds (I)”.

The invention also provides all stereoisomers which are encompassed byformula (I) and mixtures thereof. Such compounds of the formula (I)contain one or more asymmetric carbon atoms or else double bonds whichare not stated separately in the general formulae (I). The possiblestereoisomers defined by their specific three-dimensional shape, such asenantiomers, diastereomers, Z- and E-isomers, are all encompassed by theformula (I) and can be obtained from mixtures of the stereoisomers bycustomary methods or else prepared by stereoselective reactions incombination with the use of stereochemically pure starting materials.

The invention also provides all tautomers of the compounds of theformula (I) which may result from a hydrogen atom shift (for exampleketo-enol tautomers). The compound of the formula (I) also includes thetautomers, even if formally the formula (I) correctly describes only oneof the respective tautomers which are in equilibrium with one another orwhich can be converted into one another.

The compounds of the formula (I) also include all physical forms inwhich they may be present as a pure substance or, if appropriate, as amixture with other compounds, in particular also polymorphic crystalforms of the compounds of the formula (I) or salts thereof or solventadducts (for example hydrates).

Primarily for reasons of higher herbicidal activity, better selectivity,better producibility, better formulatability and/or other relevantproperties, compounds of the abovementioned formula (I) according to theinvention or their salts or their use according to the invention are ofparticular interest in which individual radicals have one of thepreferred meanings already specified or specified below, or inparticular those in which one or more of the preferred meanings alreadyspecified or specified below occur in combination.

Compounds of the formula (I) according to the invention and their usesaccording to the invention with the preferred meanings listed below ofthe symbols or chemical radicals or chemical groups in question are ofparticular interest, irrespective of the respective other radicalsaccording to the symbols (R¹)_(m), (R²)_(n), R³, R⁴ and the definitionsof m and n in formula (I) and the definitions of the radicals (orchemical groups) according to the symbols R⁵ to R¹⁹, Het¹ to Het⁷, M, R*and R**, R^(A), R^(B), R^(aa), R^(bb) and R^(cc) in the correspondingsub-meanings of radicals in the formula (I).

Preference is given to compounds (I) in which

-   (R¹)_(m) represents m substituents R¹,    -   where R¹, if m=1, or each of the substituents R¹, if m is        greater than 1, independently of the others represents halogen,        cyano, nitro, hydroxy, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl,        (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio,        (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl,        (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,        (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl,        (C₂-C₄)-haloalkenyl, (C₂-C₄)-haloalkynyl,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,        (C₃-C₆)-cycloalkyl which is optionally substituted by one or        more radicals from the group consisting of halogen and        (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally        substituted by one or more radicals from the group consisting of        halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR⁵,        C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ or Het²    -   or where in each case two groups R¹ located ortho at the ring or        R¹ and R³ together represent a group of the formula —Z¹-A*-Z² in        which    -   A* represents an alkylene group having 1 to 4 carbon atoms which        is optionally substituted by one or more radicals from the group        consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,    -   Z¹ represents a direct bond, O or S and    -   Z² represents a direct bond, O or S,    -   where the group —Z¹-A*-Z² together with the carbon atoms,        attached to the group, of the phenyl ring form a fused-on 5- or        6-membered ring,-   R⁵ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned,    preferably hydrogen, (C₁-C₄)-alkyl or the group M mentioned,-   R⁶, R⁷, R⁸, R⁹, Het¹ and Het² have the meanings mentioned,    preferably-   R⁶, R⁷, R⁸ and R⁹ independently of one another each represent    hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by    one or more radicals from the group consisting of halogen, nitro,    cyano and phenyl, or (C₃-C₆)-cycloalkyl or phenyl, where each of the    2 last-mentioned radicals in each case independently of the other is    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and    benzyl, in particular hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-haloalkyl,-   Het¹ and Het² independently of one another each represent a    saturated or partially unsaturated radical of a heterocycle having 3    to 6 ring atoms and at least one nitrogen atom as ring heteroatoms    at position 1 of the ring and optionally 1, 2 or 3 further ring    heteroatoms from the group consisting of N, O and S, where the    radical of the heterocycle is attached at the nitrogen atom in    position 1 of the ring to the remainder of the molecule of the    compound of the formula (I) and where the heterocycle is    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,    preferably the radical of a saturated heterocycle of the type    mentioned, in particular a morpholino, piperidino or pyrrolidino    group, and-   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or    1.

More preference is given to compounds (I) in which

-   (R¹)_(m) represents m substituents R¹,    -   where R¹, if m=1, or each of the substituents R¹, if m is        greater than 1, independently of the others represents halogen,        cyano, nitro, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,        (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl,        (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₃-C₆)-cycloalkyl, or a radical of the formula C(O)OR⁵,        C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ or Het²,    -   or where in each case two groups R¹ located ortho at the ring or        R¹ and R³ together represent a group of the formula —Z¹-A*-Z² in        which    -   A* represents an alkylene group having 1 to 4 carbon atoms which        is optionally substituted by one or more radicals from the group        consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,    -   Z¹ represents a direct bond, O or S and    -   Z² represents a direct bond, O or S,    -   where the group —Z¹-A*-Z² together with the carbon atoms,        attached to the group, of the phenyl ring form a fused-on 5- or        6-membered ring,-   R⁵ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned,-   R⁶, R⁷, R⁸ and R⁹ independently of one another each represent    hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl,    (C₃-C₆)-cycloalkyl or phenyl, in particular hydrogen, methyl or    ethyl,-   Het¹ and Het² independently of one another each represent a    morpholino, piperidino or pyrrolidino group and-   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or    1.

Here, more preference is given to compounds (I) in which

-   (R¹)_(m) represents m substituents R¹,-   where R¹, if m=1, or each of the substituents R¹, if m is greater    than 1, independently of the others represents halogen, cyano,    nitro, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio,    (C₁-C₂)-alkylsulphinyl, (C₁-C₂)-alkylsulphonyl, (C₁-C₂)-haloalkyl,    (C₁-C₂)-haloalkoxy, (C₁-C₂)-haloalkylthio,    (C₁-C₂)-haloalkylsulphinyl, (C₁-C₂)-haloalkylsulphonyl or    (C₁-C₂)-alkoxy-(C₁-C₂)-alkyl,    -   in particular each of the substituents R¹ independently of the        others represents halogen, such as fluorine, chlorine, bromine        or iodine, or cyano, nitro, methyl, methoxy, methylthio,        methylsulphinyl, methylsulphonyl, trifluoromethyl,        trifluoromethoxy, difluoromethoxy, trifluoroalkylthio,        trifluoromethylsulphinyl or trifluoromethylsulphonyl, in        particular cyano or halogen such as fluorine, chlorine or        bromine, and-   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or    1.

More preference is given to compounds of the formula (I) or saltsthereof in which

-   m is 0 (=the number zero, i.e. no substituents R¹ are present, i.e.    all respective free bonds at the ring are occupied by hydrogen) or    preferably-   (R¹)_(m) represents 2-bromo, 4-bromo, 6-bromo, 2-chloro, 4-chloro,    6-chloro, 2-fluoro, 4-fluoro, 6-fluoro, 2-cyano, 4-cyano, 6-cyano,    2-methyl, 4-methyl, 6-methyl, 2-ethyl, 4-ethyl, 6-ethyl, 2-CF₃,    4-CF₃, 6-CF₃, 2-methoxy, 4-methoxy, 6-methoxy, 2-ethoxy, 4-ethoxy,    6-ethoxy, 2-trifluoromethoxy, 4-trifluoromethoxy,    6-trifluoromethoxy, 2-difluoromethoxy, 4-difluoromethoxy,    6-difluoromethoxy, 2-methylthio, 4-methylthio, 6-methylthio,    2-methylsulphinyl, 4-methylsulphinyl, 6-methylsulphonyl,    2-methylsulphonyl, 4-methylsulphonyl, 6-methylsulphonyl, 2-nitro,    4-nitro, 6-nitro, 2,4-dimethyl, 2,6-dimethyl, 4,6-dimethyl,    2,4-difluoro, 2,6-difluoro, 4,6-difluoro, 2,4-dichloro,    2,6-dichloro, 4,6-dichloro, (2-Cl-4-F), (2-Cl-6-F), (4-Cl-6-F),    (2-F-4-Cl), (2-F-6-Cl), (4-F-6-Cl), 2,4,6-trifluoro or    2,4,6-trichloro, where the numbering of the radical refers to the    position of the radical at the pyridin-3-yl radical in which the    nitrogen atom is located in position 1 and the carbon atom attached    to the butyric acid parent structure is located in position 3 in the    ring.

Preference is also given to compounds (I) in which

-   (R²)_(n) represents n substituents R²,    -   where R², if n=1, or each of the substituents R², if n is        greater than 1, independently of the others represents halogen,        cyano, nitro, hydroxy, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl,        (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio,        (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl,        (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,        (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl,        (C₂-C₄)-haloalkenyl, (C₂-C₄)-haloalkynyl,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,        (C₃-C₆)-cycloalkyl which is optionally substituted by one or        more radicals from the group consisting of halogen and        (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally        substituted by one or more radicals from the group consisting of        halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR¹⁰,        C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ or Het⁴    -   or where in each case two groups R² located ortho at the ring        together are a group of the formula —Z³-A**-Z⁴ in which    -   A** represents an alkylene group having 1 to 4 carbon atoms        which is optionally substituted by one or more radicals from the        group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,    -   Z³ represents a direct bond, O or S and    -   Z⁴ represents a direct bond, O or S,    -   where the group —Z³-A**-Z⁴ together with the carbon atoms,        attached to the group, of the phenyl ring form a fused-on 5- or        6-membered ring,-   R¹⁰ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned,-   R¹¹, R¹², R¹³, R¹⁴, Het³ and Het⁴ have the meanings mentioned,    preferably-   R¹¹, R¹², R¹³ and R¹⁴ independently of one another each represent    hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by    one or more radicals from the group consisting of halogen, nitro,    cyano and phenyl, or (C₃-C₆)-cycloalkyl or phenyl, where each of the    2 last-mentioned radicals in each case independently of the other is    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and    benzyl,-   Het³ and Het⁴ independently of one another each represent a    saturated or partially unsaturated radical of a heterocycle having 3    to 6 ring atoms and at least one nitrogen atom as ring heteroatoms    at position 1 of the ring and optionally 1, 2 or 3 further ring    heteroatoms from the group consisting of N, O and S, where the    radical of the heterocycle is attached at the nitrogen atom in    position 1 of the ring to the remainder of the molecule of the    compound of the formula (I) and where the heterocycle is    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,    preferably the radical of a saturated heterocycle of the type    mentioned, in particular a morpholino, piperidino or pyrrolidino    group, and-   n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3.

Here, more preference is given to compounds (I) in which

-   (R²)_(n) represents n substituents R²,    -   where R², if n=1, or each of the substituents R², if n is        greater than 1, independently of one another represent halogen,        cyano, nitro, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,        (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl,        (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₃-C₆)-cycloalkyl, or a radical of the formula C(O)OR¹⁰,        C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ or Het⁴    -   or where in each case two groups R² located ortho at the ring        together are a group of the formula —Z³-A**-Z⁴ in which    -   A** represents an alkylene group having 1 to 4 carbon atoms        which is optionally substituted by one or more radicals from the        group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,    -   Z³ represents a direct bond, O or S and    -   Z⁴ represents a direct bond, O or S,    -   where the group —Z³-A**-Z⁴ together with the carbon atoms,        attached to the group, of the phenyl ring form a fused-on 5- or        6-membered ring,-   R¹⁰ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned,-   R¹¹, R¹², R¹³ and R¹⁴, Het³ and Het⁴ have the meanings mentioned,    preferably R¹¹, R¹², R¹³ and R¹⁴ independently of one another each    represent hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl,    (C₃-C₆)-cycloalkyl or phenyl,-   Het³ and Het⁴ independently of one another each represent a    morpholino, piperidino or pyrrolidino group and-   n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in    particular 0, 1, 2 or 3.

Here, more preference is given to compounds (I) in which

-   (R²)_(n) represents n substituents R²,-   where R², if n=1, or each of the substituents R², if n is greater    than 1, independently of the others represents halogen, cyano,    nitro, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio,    (C₁-C₂)-alkylsulphinyl, (C₁-C₂)-alkylsulphonyl, (C₁-C₂)-haloalkyl,    (C₁-C₂)-haloalkoxy, (C₁-C₂)-haloalkylthio,    (C₁-C₂)-haloalkylsulphinyl, (C₁-C₂)-haloalkylsulphonyl or    (C₁-C₂)-alkoxy-(C₁-C₂)-alkyl,    -   in particular each of the substituents R² independently of the        others represents halogen, such as fluorine, chlorine, bromine        or iodine, or cyano, nitro, methyl, methoxy, methylthio,        methylsulphinyl, methylsulphonyl, trifluoromethyl,        trifluoromethoxy, difluoromethoxy, trifluoroalkylthio,        trifluoromethylsulphinyl or trifluoromethylsulphonyl, in        particular cyano, nitro or halogen such as fluorine, chlorine or        bromine, and-   n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in    particular 0, 1, 2 or 3.

More preference is given to compounds of the formula (I) or saltsthereof in which

-   n represents 0 (=the number zero, i.e. no substituents R² are    present, i.e. all free bonds at the phenyl ring are occupied by    hydrogen) or preferably-   (R²)_(n) represents 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro,    4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-cyano, 3-cyano, 4-cyano,    2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF₃,    3-CF₃, 4-CF₃, 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy,    4-ethoxy, 2-trifluoromethoxy, 3-trifluoromethoxy,    4-trifluoromethoxy, 2-difluoromethoxy, 3-difluoromethoxy,    4-difluoromethoxy, 2-methylthio, 3-methylthio, 4-methylthio,    2-methylsulphinyl, 3-methylsulphinyl, 4-methylsulphinyl,    2-methylsulphonyl, 3-methylsulphonyl, 4-methylsulphonyl, 2-nitro,    3-nitro, 4-nitro, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl,    2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluoro,    2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro,    3,5-difluoro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro,    2,6-dichloro, 3,4-dichloro, 3,5-dichloro, (2-Cl-3-F), (2-Cl-4-F),    (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F),    (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-2-F), (4-Br-3-F),    (4-CN-3-F), (4-NO₂-3-F), 2,3,4-trifluoro, 2,3,5-trifluoro,    2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4-trichloro,    2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro, 3,4,5-trichloro    or else (2,6-difluoro-4-Cl), 2,5-dicyano, 2,6-dicyano,    (4-methoxy-3-F), (3-CN-4-F), (3-nitro-4-F), (3-CN-4-Cl),    (3-nitro-4-Cl) or (5-CN-2-F), where the numbering of the radicals    refers to the position of the radical at the phenyl-1-yl radical in    which the carbon atom attached to the 3-position at the butyric acid    parent structure has the 1-position in the ring.

More preference is given to compounds of the formula (I) or saltsthereof in which

-   (R²)_(n) represents 2-cyano, 3-cyano, 4-cyano, 2-bromo, 3-bromo,    4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro,    2-nitro, 3-nitro, 4-nitro, 2-methoxy, 3-methoxy, 4-methoxy,    2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro,    3,4-difluoro, 3,5-difluoro, 2,3-dichloro, 2,4-dichloro,    2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, (2-Cl-3-F),    (2-Cl-4-F), (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F),    (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-2-F),    (4-Br-3-F), (4-CN-3-F), (4-NO₂-3-F), 2,3,4-trifluoro,    2,3,5-trifluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro,    2,3,4-trichloro, 2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro,    3,4,5-trichloro or else (2,6-difluoro-4-Cl), 2,5-dicyano,    2,6-dicyano, (4-methoxy-3-F), (3-CN-4-F), (3-nitro-4-F),    (3-CN-4-Cl), (3-nitro-4-Cl) or (5-CN-2-F).

More preference is also given to compounds of the formula (I) or saltsthereof in which

-   (R²)_(n) represents 3-chloro, 4-chloro, 2-fluoro, 3-fluoro,    4-fluoro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro,    3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-2-F),    (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F).

Here, particular preference is given to:

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 3-chloro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 4-chloro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2-fluoro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 3-fluoro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 4-fluoro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2,3-difluoro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2,4-difluoro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2,5-difluoro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2,6-difluoro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 3,4-difluoro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 3,5-difluoro.

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (3-Cl-2-F).

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (3-Cl-4-F).

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (3-Cl-5-F).

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (3-Cl-6-F).

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (4-Cl-2-F).

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (4-Cl-3-F).

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (2,6-difluoro-4-Cl).

Preference is also given to compounds (I) in which

-   R³ represents halogen, cyano, nitro, hydroxy, (C₁-C₆)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio,    (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-haloalkynyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkyl which is optionally substituted by one or more    radicals from the group consisting of halogen and (C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkoxy which is optionally substituted by one or more    radicals from the group consisting of halogen and (C₁-C₄)-alkyl, or    a radical of the formula C(O)OR¹⁵, C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹    or Het⁶,-   R¹⁵ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned,    preferably hydrogen, (C₁-C₄)-alkyl or the group M mentioned,-   R¹⁶, R¹⁷, R¹⁸, R¹⁹, Het⁵ and Het⁶ have the meanings mentioned,    preferably-   R¹⁶, R¹⁷, R¹⁸ and R¹⁹ independently of one another each represent    hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by    one or more radicals from the group consisting of halogen, nitro,    cyano and phenyl, or (C₃-C₆)-cycloalkyl or phenyl, where each of the    2 last-mentioned radicals in each case independently of the other is    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and    benzyl, in particular hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-haloalkyl,-   Het⁵ and Het⁶ independently of one another each represent a    saturated or partially unsaturated radical of a heterocycle having 3    to 6 ring atoms and at least one nitrogen atom as ring heteroatoms    at position 1 of the ring and optionally 1, 2 or 3 further ring    heteroatoms from the group consisting of N, O and S, where the    radical of the heterocycle is attached at the nitrogen atom in    position 1 of the ring to the remainder of the molecule of the    compound of the formula (I) and where the heterocycle is    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,    preferably the radical of a saturated heterocycle of the type    mentioned, in particular a morpholino, piperidino or pyrrolidino    group.

More preference is given to compounds (I) in which

-   R³ represents halogen, cyano, nitro, hydroxy, (C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,    (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl,    (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkyl or a radical of the formula C(O)OR¹⁵,    C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹ or Het⁶,-   R¹⁵ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned,-   R¹⁶, R¹⁷, R¹⁸ and R¹⁹ independently of one another each represent    hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl,    (C₃-C₆)-cycloalkyl or phenyl, in particular hydrogen, methyl or    ethyl,-   Het⁵ and Het⁶ independently of one another each represent a    morpholino, piperidino or pyrrolidino group.

Here, more preference is given to compounds (I) in which

-   R³ represents halogen, cyano, nitro, methyl, ethyl, methoxy, ethoxy,    methylthio, ethylthio, (C₁-C₂)-alkylsulphinyl,    (C₁-C₂)-alkylsulphonyl, (C₁-C₂)-haloalkyl, (C₁-C₂)-haloalkoxy,    (C₁-C₂)-haloalkylthio, (C₁-C₂)-haloalkylsulphinyl,    (C₁-C₂)-haloalkylsulphonyl, (C₁-C₂)-alkoxy-(C₁-C₂)-alkyl or    [(C₁-C₄)-alkoxy]carbonyl, R³ represents in particular halogen, such    as fluorine, chlorine, bromine or iodine, or cyano, nitro, methyl,    methoxy, methylthio, methylsulphinyl, methylsulphonyl,    trifluoromethyl, trifluoromethoxy, difluoromethoxy,    trifluoroalkylthio, trifluoromethylsulphinyl,    trifluoromethylsulphonyl, methoxycarbonyl or ethoxycarbonyl, in    particular halogen such as fluorine, chlorine or bromine, and-   m represents 0, 1, 2 or 3, preferably 0, 1 or 2, in particular 0 or    1.

More preference is given to compounds of the formula (I) or saltsthereof in which

-   R³ represents bromine, chlorine, fluorine, cyano, methyl, nitro,    methoxycarbonyl or ethoxycarbonyl.

More preference is given to compounds of the formula (I) or saltsthereof in which

-   (R¹)_(m) and R³ together represent 5-bromo, 5-chloro, 5-fluoro,    5-cyano, 5-methyl, 5-ethyl, 5-CF₃, 5-methoxy, 5-ethoxy,    5-trifluoromethoxy, 5-difluoromethoxy, 5-methylthio,    5-methylsulphinyl, 5-methylsulphonyl, 5-nitro, 5-methoxycarbonyl,    5-ethoxycarbonyl, 2,5-difluoro, 4,5-difluoro, 5,6-difluoro,    2,5-dichloro, 4,5-dichloro, 5,6-dichloro, 2,5-dibromo, 4,5-dibromo,    5,6-dibromo, 2,5-dimethyl, 4,5-dimethyl, 5,6-dimethyl, 2,5-dicyano,    4,5-dicyano, 5,6-dicyano, (2-Cl-5-F), (4-Cl-5-F), (6-Cl-5-F),    (2-Br-5-F), (4-Br-5-F), (6-Br-5-F), (2-F-5-Cl), (4-F-5-Cl),    (6-F-5-Cl), (2-F-5-Br), (4-F-5-Br), (6-F-5-Br), (2-Br-5-Cl),    (4-Br-5-Cl), (6-Br-5-Cl), (2-Cl-5-Br), (4-Cl-5-Br), (6-Cl-5-Br),    (2-CN-5-F), (4-CN-5-F), (6-CN-5-F), (2-CH₃-5-F), (4-CH₃-5-F),    (6-CH₃-5-F), (2-OCH₃-5-F), (4-OCH₃-5-F), (6-OCH₃-5-F),    (2-OCHF₂-5-F), (4-OCHF₂-5-F), (6-OCHF₂-5-F), (2-CN-5-Cl),    (4-CN-5-Cl), (6-CN-5-Cl), (2-CH₃-5-Cl), (4-CH₃-5-Cl), (6-CH₃-5-Cl),    (2-OCH₃-5-Cl), (4-OCH₃-5-Cl), (6-OCH₃-5-Cl), (2-OCHF₂-5-Cl),    (4-OCHF₂-5-Cl), (6-OCHF₂-5-Cl),    -   (2-CN-5-Br), (4-CN-5-Br), (6-CN-5-Br), (2-CH₃-5-Br),        (4-CH₃-5-Br), (6-CH₃-5-Br),    -   (2-OCH₃-5-Br), (4-OCH₃-5-Br), (6-OCH₃-5-Br), (2-OCHF₂-5-Br),        (4-OCHF₂-5-Br), (6-OCHF₂-5-Br),    -   (2-CN-5-CH₃), (4-CN-5-CH₃), (6-CN-5-CH₃), (2-F-5-CH₃),        (4-F-5-CH₃), (6-F-5-CH₃), (2-Cl-5-CH₃), (4-Cl-5-CH₃),        (6-Cl-5-CH₃), (2-Br-5-CH₃), (4-Br-5-CH₃), (6-Br-5-CH₃),        (2-OCH₃-5-CH₃), (4-OCH₃-5-CH₃), (6-OCH₃-5-CH₃), (2-OCHF₂-5-CH₃),        (4-OCHF₂-5-CH₃), (6-OCHF₂-5-CH₃), (2-F-5-CN), (4-F-5-CN),        (6-F-5-CN), (2-Cl-5-CN), (4-Cl-5-CN), (6-Cl-5-CN), (2-Br-5-CN),        (4-Br-5-CN), (6-Br-5-CN), (2-CH₃-5-CN), (4-CH₃-5-CN),        (6-CH₃-5-CN), (2-OCH₃-5-CN), (4-OCH₃-5-CN), (6-OCH₃-5-CN),        (2-OCHF₂-5-CN), (4-OCHF₂-5-CN), (6-OCHF₂-5-CN), (2-F-5-NO₂),        (4-F-5-NO₂), (6-F-5-NO₂), (2-Cl-5-NO₂), (4-Cl-5-NO₂),        (6-Cl-5-NO₂), (2-Br-5-NO₂), (4-Br-5-NO₂), (6-Br-5-NO₂),        (2-CN-5-NO₂), (4-CN-5-NO₂), (6-CN-5-NO₂), (2-CH₃-5-NO₂),        (4-CH₃-5-NO₂), (6-CH₃-5-NO₂), (2-OCH₃-5-NO₂), (4-OCH₃-5-NO₂),        (6-OCH₃-5-NO₂), (2-OCHF₂-5-NO₂), (4-OCHF₂-5-NO₂),        (6-OCHF₂-5-NO₂), (2-F-5-CO₂CH₃), (4-F-5-CO₂CH₃), (6-F-5-CO₂CH₃),        (2-Cl-5-CO₂CH₃), (4-Cl-5-CO₂CH₃), (6-Cl-5-CO₂CH₃),        (2-Br-5-CO₂CH₃), (4-Br-5-CO₂CH₃), (6-Br-5-CO₂CH₃),        (2-CN-5-CO₂CH₃), (4-CN-5-CO₂CH₃), (6-CN-5-CO₂CH₃),        (2-CH₃-5-CO₂CH₃), (4-CH₃-5-CO₂CH₃), (6-CH₃-5-CO₂CH₃),        (2-OCH₃-5-CO₂CH₃), (4-OCH₃-5-CO₂CH₃), (6-OCH₃-5-CO₂CH₃),        (2-OCHF₂-5-CO₂CH₃), (4-OCHF₂-5-CO₂CH₃) or (6-OCHF₂-5-CO₂CH₃).

More preference is here given to compounds of the formula (I) or saltsthereof in which

-   (R¹)_(m) and R³ together represent 5-bromo, 5-chloro, 5-fluoro,    5-cyano, 5-methyl, 5-ethyl, 5-CF₃, 5-methoxy, 5-nitro,    5-methoxycarbonyl, 5-ethoxycarbonyl, 2,5-difluoro, 4,5-difluoro,    5,6-difluoro, 5,6-dichloro, 5,6-dibromo, 5,6-dimethyl, 5,6-dicyano,    (6-Cl-5-F), (6-Br-5-F), (2-F-5-Cl), (4-F-5-Cl), (6-F-5-Cl),    (2-F-5-Br), (4-F-5-Br), (6-F-5-Br), (6-Br-5-Cl), (6-Cl-5-Br),    (6-CN-5-F), (6-CH₃-5-F), (6-OCH₃-5-F), (6-OCHF₂-5-F), (6-CN-5-Cl),    (6-CH₃-5-Cl), (6-OCH₃-5-Cl), (6-OCHF₂-5-Cl), (6-CN-5-Br),    (6-CH₃-5-Br), (6-OCH₃-5-Br), (6-OCHF₂-5-Br), (6-CN-5-CH₃),    (2-F-5-CH₃), (4-F-5-CH₃), (6-F-5-CH₃), (6-Cl-5-CH₃), (6-Br-5-CH₃),    (6-OCH₃-5-CH₃), (6-OCHF₂-5-CH₃), (2-F-5-CN), (4-F-5-CN), (6-F-5-CN),    (6-Cl-5-CN), (6-Br-5-CN), (6-CH₃-5-CN), (6-OCH₃-5-CN),    (6-OCHF₂-5-CN), (2-F-5-NO₂), (4-F-5-NO₂), (6-F-5-NO₂), (6-Cl-5-NO₂),    (6-Br-5-NO₂), (6-CN-5-NO₂), (6-CH₃-5-NO₂), (6-OCH₃-5-NO₂),    (6-OCHF₂-5-NO₂), (2-F-5-CO₂CH₃), (4-F-5-CO₂CH₃), (6-F-5-CO₂CH₃),    (6-Cl-5-CO₂CH₃), (6-Br-5-CO₂CH₃), (6-CN-5-CO₂CH₃), (6-CH₃-5-CO₂CH₃),    (6-OCH₃-5-CO₂CH₃) or (6-OCHF₂-5-CO₂CH₃).

More preference is given to:

Compounds of the formula (I) or salts thereof in which m=0 and (R²)_(n)represents 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro,2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro,3,5-difluoro, (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F)or (4-Cl-3-F) or else (2,6-difluoro-4-Cl), 3-cyano, 4-cyano, 3-nitro or4-nitro and R³ represents fluorine, chlorine, bromine, methyl, cyano,nitro or methoxycarbonyl.Compounds of the formula (I) or salts thereof in which (R¹)_(m)=2-F,2-Cl, 4-F, 4-Cl, 6-F, 6-Cl, 2-Br, 4-Br, 6-Br, 2-CN, 4-CN, 6-CN,2-methyl, 4-methyl, 6-methyl, 2-ethyl, 4-ethyl, 6-ethyl, 2-methoxy,4-methoxy, 6-methoxy, 2-ethoxy, 4-ethoxy, 6-ethoxy, 2-difluoromethoxy,4-difluoromethoxy, 6-difluoromethoxy, 2-trifluoromethoxy,4-trifluoromethoxy or 6-trifluoromethoxy and (R²)_(n) represents3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2,3-difluoro,2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro,(3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3-F)or else (2,6-difluoro-4-Cl), 3-cyano, 4-cyano, 3-nitro or 4-nitro and R³represents fluorine, chlorine, bromine, methyl, cyano, nitro,methoxycarbonyl or ethoxycarbonyl.Compounds of the formula (I) or salts thereof in which (R¹)_(m)=2-F,2-Cl, 4-F, 4-Cl, 6-F, 6-Cl, 6-Br, 6-CN, 6-methyl, 6-methoxy or6-difluoromethoxy and (R²)_(n) represents 3-chloro, 4-chloro, 2-fluoro,3-fluoro, 4-fluoro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro,2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3-Cl-2-F), (3-Cl-4-F),(3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3-F) or else(2,6-difluoro-4-Cl), 3-cyano, 4-cyano, 3-nitro or 4-nitro and R³represents fluorine, chlorine, bromine, methyl, cyano, nitro ormethoxycarbonyl.

In general, from among the compounds having the abovementioned meaningsfor individual groups or combinations of groups (R¹)_(m), (R²)_(n) andR³, preference is given to those in which the remaining groups orcombinations of groups in the compounds are defined according to themeanings mentioned as preferred.

Preference is also given to compounds (I) in which

-   M represents an equivalent of a cation, preferably a metal ion    equivalent, an ammonium ion which is optionally substituted by 1 to    4 identical or different radicals from the group consisting of    (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, phenyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl and phenyl-(C₁-C₄)-alkyl, in    particular (C₁-C₄)-alkyl, or a tertiary sulphonium ion which is    preferably substituted by 3 identical or different radicals from the    group consisting of (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, phenyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl and phenyl-(C₁-C₄)-alkyl, in    particular (C₁-C₄)-alkyl.

Preference is given to the compounds of the formula (I) according to theinvention, preferably of the formula (Ia), or salts thereof in which

-   R⁴ represents hydrogen, alkyl, alkenyl or alkynyl, where each of the    3 last-mentioned radicals is unsubstituted or substituted and,    including substituents, has up to 30 carbon atoms, preferably up to    24 carbon atoms, in particular up to 20 carbon atoms, or    -   represents cycloalkyl, cycloalkenyl, cycloalkynyl or aryl, where        each of the 4 last-mentioned radicals is unsubstituted or        substituted and, including substituents, has up to 30 carbon        atoms, preferably up to 24 carbon atoms, in particular up to 20        carbon atoms, or    -   represents a heterocyclyl radical having 3 to 9 ring atoms which        contains 1 to 4 heteroatoms from the group consisting of N, O        and S, which is unsubstituted or substituted and which,        including substituents, has 1 to 30 carbon atoms, preferably 1        to 24 carbon atoms, in particular 1 to 20 carbon atoms.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which R⁴ represents hydrogen.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R⁴ represents H, (C₁-C₁₈)-alkyl, (C₂-C₁₈)-alkenyl or    (C₂-C₁₈)-alkynyl, where each of the 3 last-mentioned radicals is    unsubstituted or substituted and, including substituents, has up to    30 carbon atoms, preferably up to 24 carbon atoms, in particular up    to 20 carbon atoms, or    -   represents (C₃-C₉)-cycloalkyl, (C₅-C₉)-cycloalkenyl,        (C₅-C₉)-cycloalkynyl or phenyl, where each of the 4        last-mentioned radicals is unsubstituted or substituted and,        including substituents, has up to 30 carbon atoms, preferably up        to 24 carbon atoms, in particular up to 20 carbon atoms.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R⁴ represents hydrogen, (C₁-C₁₈)-alkyl, (C₂-C₁₈)-alkenyl or    (C₂-C₁₈)-alkynyl, where each of the 3 last-mentioned radicals is    unsubstituted or substituted by one or more radicals from the group    consisting of the radicals [subgroups (a)-(d)]    -   (a) halogen, cyano, thio, nitro, hydroxy, carboxy,        (C₁-C₈)-alkoxy, (C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy,        (C₁-C₈)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,        (C₁-C₈)-alkylthio, (C₂-C₈)-alkenylthio, (C₂-C₈)-alkynylthio,        (C₁-C₈)-haloalkylthio, (C₂-C₈)-haloalkenylthio,        (C₂-C₈)-haloalkynylthio, (C₁-C₈)-alkylsulphinyl,        (C₂-C₈)-alkenylsulphinyl, (C₂-C₈)-alkynylsulphinyl,        (C₁-C₈)-haloalkylsulphinyl, (C₂-C₈)-haloalkenylsulphinyl,        (C₂-C₈)-haloalkynylsulphinyl, (C₁-C₈)-alkylsulphonyl,        (C₂-C₈)-alkenylsulphonyl, (C₂-C₈)-alkynylsulphonyl,        (C₁-C₈)-haloalkylsulphonyl, (C₂-C₈)-haloalkenylsulphonyl,        (C₂-C₈)-haloalkynylsulphonyl, radicals of the formula —NR*R**,        where R* and R** are defined as above or below, and        (C₃-C₈)-cycloalkyl, (C₅-C₈)-cycloalkenyl, (C₅-C₈)-cycloalkynyl,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,        (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl-S(O)_(p)—,        (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,        (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl-S(O)_(p)—,        (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy,        (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl-S(O)_(p)—,        (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-S(O)_(p)—,        (C₅-C₈)-cycloalkenyloxy, (C₅-C₈)-cycloalkenyl-S(O)_(p)—,        (C₅-C₈)cycloalkynyloxy, (C₅-C₈)-cycloalkynyl-S(O)_(p)—,        (C₃-C₈)-cycloalkoxy-(C₁-C₆)-alkoxy,        (C₃-C₈)-cycloalkoxy-(C₁-C₆)-alkyl-S(O)_(p)—, phenyl,        phenyl-(C₁-C₆)-alkoxy, phenoxy, phenyl-S(O)_(p)—,        phenyl-(C₁-C₆)-alkyl-S(O)_(p)—, phenoxy-(C₁-C₆)-alkoxy,        phenoxy-(C₁-C₆)-alkyl-S(O)_(p)—, a radical Het⁷, Het⁷-S(O)_(p)—,        Het⁷-(C₁-C₆)-alkoxy, Het⁷-O—, Het⁷-O—(C₁-C₆)-alkoxy, where the        heterocyclic radical Het⁷ is defined as above or below,        -   where each of the 29 last-mentioned radicals is            unsubstituted in the acyclic moiety or substituted by one or            more identical or different radicals R^(A) and is            unsubstituted in the cyclic moiety or substituted by one or            more identical or different radicals R^(B) and p            independently of the others in each case represents 0, 1 or            2, and        -   preferably the radicals (a)        -   halogen, cyano, nitro, hydroxy, carboxy, (C₁-C₆)-alkoxy,            (C₁-C₈)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,            (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,            (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,        -   (C₁-C₆)-alkylsulphonyl, (C₁-C₈)-haloalkylsulphonyl,        -   (C₃-C₈)-cycloalkyl,        -   (C₅-C₈)-cycloalkenyl,        -   (C₅-C₈)-cycloalkynyl,        -   (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,        -   (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,        -   (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy,        -   (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkylthio,        -   (C₃-C₈)-cycloalkylsulphinyl, (C₃-C₈)-cycloalkylsulphonyl,        -   (C₃-C₈)-cycloalkoxy-(C₁-C₆)-alkoxy,        -   phenyl, phenoxy, phenylthio, phenylsulphinyl,            phenylsulphonyl,        -   phenyl-(C₁-C₆)-alkoxy, phenyl-(C₁-C₆)-alkylthio,        -   phenyl-(C₁-C₆)-alkylsulphinyl,            phenyl-(C₁-C₆)-alkylsulphonyl,        -   phenoxy-(C₁-C₆)-alkoxy, phenoxy-(C₁-C₆)-alkylthio,        -   phenoxy-(C₁-C₆)-alkylsulphinyl and            phenoxy-(C₁-C₆)-alkylsulphyl,            -   where each of the radicals mentioned with cyclic                moieties is unsubstituted in the acyclic moiety or                substituted by one or more identical or different                radicals R^(A) and is unsubstituted in the cyclic moiety                or substituted by one or more identical or different                radicals R^(B),    -   (b) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),        —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),        —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,        —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,        —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),        —P(═O)(OR^(c))(R^(D)), —P(═O)(OR^(c))(OR^(D)) or        —O—P(═O)(OR^(c))(OR^(D)), preferably a radical of the formula        —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(c) or        —O—C(═O)—O—R^(C), in particular a radical of the formula        —C(═O)—O—R^(C), —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C),        -   where R*, R**, R^(C) and R^(D) are as defined below,        -   preferably the radicals (b1)        -   [(C₁-C₈)-alkoxy]carbonyl, [(C₁-C₈)-alkoxy]thiocarbonyl,            [(C₂-C₈)-alkenyloxy]carbonyl, [(C₂-C₈)-alkynyloxy]carbonyl,            [(C₁-C₈)-alkylthio]carbonyl, [(C₂-C₈)-alkenylthio]carbonyl,            [(C₂-C₈)-alkynylthio]carbonyl, (C₁-C₈)-alkanoyl,            [(C₂-C₈)-alkenyl]carbonyl, [(C₂-C₈)-alkynyl]carbonyl,            [(C₁-C₈)-alkyl]carbonylamino,            [(C₂-C₈)-alkenyl]carbonylamino,            [(C₂-C₈)-alkynyl]carbonylamino,            [(C₁-C₆)-alkoxy]carbonylamino,            [(C₂-C₈)-alkenyloxy]carbonylamino,            [(C₂-C₈)-alkynyloxy]carbonylamino,            [(C₁-C₈)-alkylamino]carbonylamino,            [(C₁-C₆)-alkyl]carbonyloxy, [(C₂-C₆)-alkenyl]carbonyloxy,            [(C₂-C₆)-alkynyl]carbonyloxy, [(C₁-C₈)-alkoxy]carbonyloxy,            [(C₂-C₈)-alkenyloxy]carbonyloxy and            [(C₂-C₈)-alkynyloxy]carbonyloxy, where each of the 23            last-mentioned radicals is unsubstituted or substituted by            one or more radicals from the group consisting of halogen,            NO₂, (C₁-C₄)-alkoxy and optionally halogen-, CN, NO₂—,            (C₁-C₄)-alkyl-, (C₁-C₄)-alkoxy- and            (C₁-C₄)-alkylthio-substituted phenyl, and preferably the            radicals (b2)        -   (C₃-C₈)-cycloalkylcarbonyl,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyl,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyl,        -   (C₃-C₈)-cycloalkoxycarbonyl,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyl,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyl,        -   (C₃-C₈)-cycloalkylcarbonyloxy,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₃-C₈)-cycloalkoxycarbonyloxy,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₃-C₈)-cycloalkylcarbonylamino,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonylamino,        -   (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonylamino,        -   (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonylamino,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonylamino,        -   (C₃-C₈)-cycloalkoxycarbonylamino,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonylamino and        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonylamino,        -   phenylcarbonyl,        -   phenyl-[(C₁-C₆)-alkyl]carbonyl,        -   phenyl-[(C₁-C₆)-alkoxy]carbonyl,        -   phenoxycarbonyl,        -   phenoxy-[(C₁-C₆)-alkyl]carbonyl,        -   phenoxy-[(C₁-C₆)-alkoxy]carbonyl,        -   phenylcarbonyloxy,        -   phenyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   phenyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   phenoxycarbonyloxy,        -   phenoxy-[(C₁-C₆)-alkyl]carbonyloxy,        -   phenoxy-[(C₁-C₆)-alkoxy]carbonyloxy,        -   phenylcarbonylamino,        -   phenyl-[(C₁-C₆)-alkyl]carbonylamino,        -   phenyl-[(C₁-C₆)-alkoxy]carbonylamino,        -   phenoxycarbonylamino,        -   phenoxy-[(C₁-C₆)-alkyl]carbonylamino,        -   phenoxy-[(C₁-C₆)-alkoxy]carbonylamino,        -   where each of the 42 last-mentioned radicals is optionally            fused in the cyclic moiety with a carbocyclic or            heterocyclic ring, preferably a carbocyclic ring having 3 to            6 carbon atoms or a heterocyclic ring having 5 or 6 ring            atoms and 1 to 3 ring heteroatoms from the group consisting            of N, O and S, preferably benzo-fused, and unsubstituted at            the ring or at the polycyclic system or substituted by one            or more radicals from the group consisting of halogen,            (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,            (C₁-C₄)-haloalkoxy and nitro, and    -   (c) radicals of the formulae —SiR′₃, —O—SiR′₃,        (R′)₃Si—(C₁-C₆)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,        —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OR)₂, in which each of the        radicals R′ independently of the others represents H,        (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted        by one or more radicals from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-haloalkoxy and nitro or at two adjacent positions by a        (C₂-C₆)-alkylene bridge, and q represents an integer from 0 to        6, and    -   (d) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy,        -   in which each of the radicals R″ independently of the others            represents H or (C₁-C₄)-alkyl or together the radicals            represent a (C₁-C₆)-alkylene group and R′″ represents H or            (C₁-C₄)-alkyl,    -   or-   R⁴ represents (C₃-C₉)-cycloalkyl, (C₅-C₉)-cycloalkenyl,    (C₅-C₉)-cycloalkynyl or phenyl,    -   where each of the 4 last-mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        the radicals [subgroups (a′)-(e′)]    -   (a′) halogen, cyano, thio, nitro, hydroxy, carboxy,        (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl, (C₂-C₈)-alkynyl,        (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy, (C₂-C₈)-alkenyloxy,        (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₈)-alkylthio,        (C₂-C₈)-alkenylthio, (C₂-C₈)-alkynylthio and radicals of the        formulae —NR*R**, where the radicals R* and R** are defined        below,    -   (b′) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),        —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),        —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,        —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,        —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),        —P(═O)(OR^(c))(R^(D)), —P(═O)(OR^(c))(OR^(D)) and        —O—P(═O)(OR^(c))(OR^(D)),        -   preferably a radical of the formula —C(═O)—R^(C),            —C(═O)—O—R^(C), —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C), in            particular a radical of the formula —C(═O)—O—R^(C),            —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C),        -   where R*, R**, R^(C) and R^(D) are as defined below,        -   and preferably the radicals (b1′)        -   [(C₁-C₈)-alkoxy]carbonyl, [(C₁-C₈)-alkoxy]thiocarbonyl,            [(C₂-C₈)-alkenyloxy]carbonyl, [(C₂-C₈)-alkynyloxy]carbonyl,            [(C₁-C₈)-alkylthio]carbonyl, [(C₂-C₈)-alkenylthio]carbonyl,            [(C₂-C₈)-alkynylthio]carbonyl, (C₁-C₈)-alkanoyl,            [(C₂-C₈)-alkenyl]carbonyl, [(C₂-C₈)-alkynyl]carbonyl,            (C₁-C₄)-alkylimino, (C₁-C₄)-alkoxyimino,            [(C₁-C₈)-alkyl]carbonylamino,            [(C₂-C₈)-alkenyl]carbonylamino,            [(C₂-C₈)-alkynyl]carbonylamino,            [(C₁-C₈)-alkoxy]carbonylamino,            [(C₂-C₈)-alkenyloxy]carbonylamino,            [(C₂-C₈)-alkynyloxy]carbonylamino,            [(C₁-C₈)-alkylamino]carbonylamino,            [(C₁-C₆)-alkyl]carbonyloxy, [(C₂-C₆)-alkenyl]carbonyloxy,            [(C₂-C₆)-alkynyl]carbonyloxy, [(C₁-C₈)-alkoxy]carbonyloxy,            [(C₂-C₈)-alkenyloxy]carbonyloxy,            [(C₂-C₈)-alkynyloxy]carbonyloxy, (C₁-C₈)-alkylsulphinyl and            (C₁-C₈)-alkylsulphonyl, where each of the 27 last-mentioned            radicals is unsubstituted or substituted by one or more            radicals from the group consisting of halogen, NO₂,            (C₁-C₄)-alkoxy and optionally substituted phenyl, and            preferably the radicals (b2′)        -   (C₃-C₈)-cycloalkylcarbonyl,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyl,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyl,        -   (C₃-C₈)-cycloalkoxycarbonyl,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyl,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyl,        -   (C₃-C₈)-cycloalkylcarbonyloxy,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₃-C₈)-cycloalkoxycarbonyloxy,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₃-C₈)-cycloalkylcarbonylamino,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonylamino,        -   (C₅-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonylamino,        -   (C₅-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonylamino,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonylamino,        -   (C₃-C₈)-cycloalkoxycarbonylamino,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonylamino and        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonylamino,        -   phenylcarbonyl,        -   phenyl-[(C₁-C₆)-alkyl]carbonyl,        -   phenyl-[(C₁-C₆)-alkoxy]carbonyl,        -   phenoxycarbonyl,        -   phenoxy-[(C₁-C₆)-alkyl]carbonyl,        -   phenoxy-[(C₁-C₆)-alkoxy]carbonyl,        -   phenylcarbonyloxy,        -   phenyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   phenyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   phenoxycarbonyloxy,        -   phenoxy-[(C₁-C₆)-alkyl]carbonyloxy,        -   phenoxy-[(C₁-C₆)-alkoxy]carbonyloxy,        -   phenylcarbonylamino,        -   phenyl-[(C₁-C₆)-alkyl]carbonylamino,        -   phenyl-[(C₁-C₆)-alkoxy]carbonylamino,        -   phenoxycarbonylamino,        -   phenoxy-[(C₁-C₆)-alkyl]carbonylamino,        -   phenoxy-[(C₁-C₆)-alkoxy]carbonylamino,        -   where each of the 42 last-mentioned radicals is optionally            fused in the cyclic moiety with a carbocyclic or            heterocyclic ring, preferably a carbocyclic ring having 3 to            6 carbon atoms or a heterocyclic ring having 5 or 6 ring            atoms and 1 to 3 ring heteroatoms from the group consisting            of N, O and S, preferably benzo-fused, and unsubstituted at            the ring or at the polycyclic system or substituted by one            or more radicals from the group consisting of halogen,            (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,            (C₁-C₄)-haloalkoxy and nitro, and    -   (c′) radicals of the formulae —SiR′₃, —O—SiR′₃,        (R′)₃Si—(C₁-C₆)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,        —CH(OR′)₂ and —O—(CH₂)q-CH(OR′)₂,        -   in which each of the radicals R′ independently of the others            represents H, (C₁-C₄)-alkyl or phenyl, which is            unsubstituted or substituted by one or more radicals from            the group consisting of halogen, (C₁-C₄)-alkyl,            (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy and            nitro or at two adjacent positions by a (C₂-C₆)-alkylene            bridge, and q represents an integer from 0 to 6, and    -   (d′) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy,        -   in which each of the radicals R″ independently of the others            is H or (C₁-C₄)-alkyl or together the radicals are a            (C₁-C₆)-alkylene group and R′″ is H or (C₁-C₄)-alkyl, and    -   (e′) a radical of the formula Het⁷ which is unsubstituted or        substituted by one or more identical or different radicals        R^(B),    -   or-   R⁴ represents a polycyclic radical based on (C₃-C₉)-cycloalkyl,    (C₅-C₉)-cycloalkenyl, (C₅-C₉)-cycloalkynyl or phenyl, where the base    ring is fused with a carbocyclic or heterocyclic ring, preferably a    5- or 6-membered ring having 0 or 1 to 3 ring heteroatoms from the    group consisting of N, O and S, preferably benzo-fused, and where    the base ring or the polycyclic system is unsubstituted or    substituted by one or more identical or different radicals R^(B),    preferably unsubstituted or substituted by one or more radicals from    the group consisting of halogen, cyano, nitro, hydroxy, carboxy,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy,    (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₆)-alkylthio,    (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, [(C₁-C₈)-alkoxy]carbonyl,    [(C₁-C₆)-haloalkoxy]carbonyl and oxo, or-   R⁴ represents a heterocyclic radical Het⁷ which is unsubstituted in    the ring or in the polycyclic system or substituted by one or more    identical or different radicals R^(B), preferably unsubstituted or    substituted by one or more radicals from the group consisting of    halogen, cyano, thio, nitro, hydroxy, carboxy, (C₁-C₆)-alkyl,    (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,    (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy,    (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkoxy, [(C₁-C₈)-alkoxy]carbonyl,    [(C₁-C₆)-haloalkoxy]carbonyl and oxo,-   where in the radicals mentioned above and in the radicals below-   Het⁷ in each case independently of the others is a saturated,    partially unsaturated or heteroaromatic monocyclic heterocyclyl    radical having 3 to 9 ring atoms, preferably having 5 or 6 ring    atoms, or a 9- or 10-membered bicyclic heterocycle which contains 1,    2, 3 or 4 heteroatoms selected from the group consisting of O, N and    S, preferably a 5- or 6-membered heterocycle having 1 to 3 ring    heteroatoms from the group consisting of N, O and S which is    optionally also fused to a carbocyclic or heterocyclic ring,    preferably a carbocyclic ring having 3 to 6 carbon atoms or a    heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring    heteroatoms from the group consisting of N, O and S, preferably    optionally benzo-fused,-   R*, R** independently of one another (i.e. also of other groups    NR*R**) each represent H, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl,    (C₂-C₈)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,    [(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,    [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, phenyl-(C₁-C₄)-alkyl,    where each of the 4 last-mentioned radicals is optionally    substituted in the cycle by one or more identical or different    radicals R^(bb), or-   R* and R** together with the nitrogen atom represent a 3- to    8-membered heterocycle which, in addition to the nitrogen atom, may    contain one or two further ring heteroatoms from the group    consisting of N, O and S and which may be unsubstituted or    substituted by one or more radicals from the group consisting of    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,-   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy,-   R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₆)-alkyl,    (C₁-C₄)-haloalkyl, cyano-(C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkyl,    nitro-(C₁-C₄)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy,    (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkoxy,    (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,    (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,    (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of the    formula R^(aa)—C(═O)— or R^(aa)—C(═O)—(C₁-C₆)alkyl, the radicals    R^(aa) being defined below, —NR*R**, R* and R** being defined below,    tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkoxy,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkoxy,    phenyl, phenyl-(C₁-C₆)-alkyl, phenoxy, phenoxy-(C₁-C₆)-alkyl,    phenylamino, phenylamino-(C₁-C₆)-alkyl or a 5- or 6-membered    monocyclic or 9- or 10-membered bicyclic heterocycle which contains    1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N    and S, where each of the 11 last-mentioned radicals is optionally    substituted in the cyclic moiety by one or more identical or    different radicals R^(bb),-   R^(C), R^(D) are each independently of one another (also    independently of radicals R^(C), R^(D) in other groups)    -   hydrogen, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl or (C₂-C₈)-alkynyl,        -   where each of the 3 last-mentioned radicals is unsubstituted            or substituted by one or more radicals from the group            consisting of halogen, cyano, nitro, hydroxy,            (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy,            (C₁-C₈)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,            (C₁-C₈)-alkylthio, (C₁-C₈)-haloalkylthio,            (C₁-C₈)-alkylsulphinyl, (C₁-C₈)-haloalkylsulphinyl,            (C₁-C₈)-alkylsulphonyl, (C₁-C₈)-haloalkylsulphonyl and            tri-[(C₁-C₄)-alkyl]silyl,    -   or    -   (C₃-C₈)-cycloalkyl, (C₅-C₈)-cycloalkenyl, (C₅-C₈)-cycloalkynyl,        phenyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl, phenyl-(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkyloxy-(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkyl-S(O)_(p)—(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkenyloxy-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkynyloxy-(C₁-C₆)-alkyl, phenoxy-(C₁-C₆)-alkyl,        phenyl-S(O)_(p)—(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkylamino-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkenylamino-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkynylamino-(C₁-C₆)-alkyl,        phenylamino-(C₁-C₆)-alkyl, Het⁷, Het⁷-(C₁-C₆)-alkyl,        Het⁷-O—(C₁-C₆)-alkyl or Het⁷-S(O)_(p)—(C₁-C₆)-alkyl, where Het⁷        has the meaning mentioned,        -   where each of the 22 last-mentioned radicals is            unsubstituted in the acyclic moiety or substituted by one or            more identical or different radicals R^(A) and is            unsubstituted in the cyclic moiety or substituted by one or            more identical or different radicals R^(B) and p            independently of the others in each case represents 0, 1 or            2,-   R^(aa) independently of one another each represent hydrogen, OH,    (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-haloalkoxy-(C₁-C₆)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₆)-alkoxy,    (C₃-C₆)-alkenyloxy, (C₃-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₃-C₆)-alkenyloxy-(C₁-C₆)-alkoxy, (C₃-C₆)-alkynyloxy,    (C₃-C₆)-alkynyloxy-(C₁-C₆)-alkyl, (C₃-C₆)-alkynyloxy-(C₁-C₆)-alkoxy,    —NR*R*, where R* and R** are as defined above,    tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkyl,    tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkoxy, (C₅-C₆)-cycloalkenyl,    (C₅-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₆)-cycloalkenyloxy,    (C₅-C₆)-cycloalkynyl, (C₅-C₆)-cycloalkynyl-(C₁-C₆)-alkyl,    (C₅-C₆)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₆)-alkyl,    phenyl-(C₁-C₆)-alkoxy, phenoxy, phenoxy-(C₁-C₆)-alkyl,    phenoxy-(C₁-C₆)-alkoxy, phenylthio, phenyl-S(O)_(p)—(C₁-C₆)-alkyl,    phenyl-S(O)_(p)—(C₁-C₆)-alkoxy, where p independently of the others    in each case represents 0, 1 or 2, phenylamino,    phenylamino-(C₁-C₁)-alkyl, phenylamino-(C₁-C₆)-alkoxy or a 5- or    6-membered monocyclic or 9- or 10-membered bicyclic heterocycle    which is optionally attached via an alkylene group or an alkoxy    group and contains 1, 2, 3 or 4 heteroatoms selected from the group    consisting of O, N and S, where each of the 20 last-mentioned    radicals is optionally substituted in the cyclic moiety by one or    more identical or different radicals R^(cc), and-   R^(bb) and R^(cc) independently of one another each represent    halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or    (C₁-C₄)-haloalkoxy.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R⁴ represents hydrogen, (C₁-C₁₈)-alkyl, (C₂-C₁₈)-alkenyl or    (C₂-C₁₈)-alkynyl, preferably H, (C₁-C₁₂)-alkyl, (C₂-C₁₂)-alkenyl or    (C₂-C₁₂)-alkynyl, in particular H, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl or    (C₂-C₈)-alkynyl, more preferably H or (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl    or (C₂-C₆)-alkynyl, more preferably (C₁-C₄)-alkyl, where each of the    13 last-mentioned radicals containing carbon atoms is unsubstituted    or substituted by one or more radicals from the group consisting of    the radicals [subgroups (a)-(d)]    -   (a) halogen, cyano, thio, nitro, hydroxy, carboxy,        (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy,        (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,        (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,        (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio,        (C₂-C₆)-haloalkynylthio, (C₁-C₆)-alkylsulphinyl,        (C₂-C₆)-alkenylsulphinyl, (C₂-C₆)-alkynylsulphinyl,        (C₁-C₆)-haloalkylsulphinyl, (C₂-C₆)-haloalkenylsulphinyl,        (C₂-C₆)-haloalkynylsulphinyl, (C₁-C₆)-alkylsulphonyl,        (C₂-C₆)-alkenylsulphonyl, (C₂-C₆)-alkynylsulphonyl,        (C₁-C₆)-haloalkylsulphonyl, (C₂-C₆)-haloalkenylsulphonyl,        (C₂-C₆)-haloalkynylsulphonyl, radicals of the formula —NR*R**,        where R* and R** are defined below, and (C₃-C₆)-cycloalkyl,        (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl,        (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy,        (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkoxy,        (C₅-C₆)-cycloalkynyl-(C₁-C₄)-alkoxy, (C₃-C₆)-cycloalkoxy,        (C₅-C₆)-cycloalkenyloxy, (C₅-C₆)-cycloalkynyloxy,        (C₃-C₆)-cycloalkoxy-(C₁-C₄)-alkoxy, phenyl,        phenyl-(C₁-C₆)-alkoxy, phenoxy, phenoxy-(C₁-C₄)-alkoxy,        phenyl-S(O)_(p)—, phenyl-(C₁-C₆)-alkyl-S(O)_(p)—,        phenyloxy-(C₁-C₆)-alkyl-S(O)_(p)—, a radical Het⁷,        Het⁷-(C₁-C₆)-alkoxy, Het⁷-O—, Het⁷-O—(C₁-C₄)-alkoxy,        Het⁷-(C₁-C₆)-alkoxy, Het⁷-S(O)_(p)—,        Het⁷-O—(C₁-C₄)-alkyl-S(O)_(p)—, where the heterocyclic radical        Het⁷ is defined as above or below,        -   where each of the 24 last-mentioned radicals is            unsubstituted in the acyclic moiety or substituted by one or            more identical or different radicals R^(A) and is            unsubstituted in the cyclic moiety or substituted by one or            more identical or different radicals R^(B) and p            independently of the others in each case represents 0, 1 or            2,        -   and        -   preferably the radicals (a1)        -   halogen, cyano, nitro, hydroxy, carboxy, (C₁-C₆)-alkoxy,            (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,            (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,            (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,            (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl,            (C₅-C₆)-cycloalkynyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy,            (C₅-C₄)-cycloalkenyl-(C₁-C₄)-alkoxy,            (C₅-C₄)-cycloalkynyl-(C₁-C₄)-alkoxy, (C₃-C₄)-cycloalkoxy,            (C₃-C₄)-cycloalkoxy-(C₁-C₄)-alkoxy, phenyl,            phenyl-(C₁-C₄)-alkoxy, phenoxy and phenoxy-(C₁-C₄)-alkoxy,            phenylthio, phenylsulphinyl, phenylsulphonyl,            -   where each of the radicals (a1) is unsubstituted in the                acyclic moiety or substituted by one or more identical                or different radicals R^(A) and is unsubstituted in the                cyclic moiety or substituted by one or more identical or                different radicals R^(B),    -   (b) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),        —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),        —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,        —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,        —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),        —P(═O)(OR^(c))(R^(D)), —P(═O)(OR^(c))(OR^(D)) and        —O—P(═O)(OR^(c))(OR^(D)), preferably a radical of the formula        —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(c) or        —O—C(═O)—O—R^(C), in particular a radical of the formula        —C(═O)—O—R^(C), —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C),        -   where R*, R**, R^(C) and R^(D) are as defined below,        -   preferably the radicals (b1)        -   [(C₁-C₆)-alkoxy]carbonyl, [(C₁-C₆)-alkoxy]thiocarbonyl,            [(C₂-C₆)-alkenyloxy]carbonyl, [(C₂-C₈)-alkynyloxy]carbonyl,            [(C₁-C₆)-alkylthio]carbonyl, [(C₂-C₆)-alkenylthio]carbonyl,            [(C₂-C₆)-alkynylthio]carbonyl, (C₁-C₆)-alkanoyl,            [(C₂-C₆)-alkenyl]carbonyl, [(C₂-C₆)-alkynyl]carbonyl,            [(C₁-C₆)-alkyl]carbonylamino,            [(C₂-C₆)-alkenyl]carbonylamino,            [(C₂-C₆)-alkynyl]carbonylamino,            [(C₁-C₆)-alkoxy]carbonylamino,            [(C₂-C₆)-alkenyloxy]carbonylamino,            [(C₂-C₆)-alkynyloxy]carbonylamino,            [(C₁-C₆)-alkylamino]carbonylamino,            [(C₁-C₆)-alkyl]carbonyloxy, [(C₂-C₆)-alkenyl]carbonyloxy,            [(C₂-C₆)-alkynyl]carbonyloxy, [(C₁-C₆)-alkoxy]carbonyloxy,            [(C₂-C₆)-alkenyloxy]carbonyloxy and            [(C₂-C₆)-alkynyloxy]carbonyloxy,        -   where each of the 23 last-mentioned radicals is            unsubstituted or substituted by one or more radicals from            the group consisting of halogen, NO₂, (C₁-C₄)-alkoxy and            optionally halogen-, CN, NO₂, (C₁-C₄)-alkyl-,            (C₁-C₄)-alkoxy- and (C₁-C₄)-alkylthio-substituted phenyl,            and preferably the radicals (b2)        -   (C₃-C₆)-cycloalkylcarbonyl,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyl,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyl,        -   (C₃-C₆)-cycloalkoxycarbonyl,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyl,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyl,        -   (C₃-C₆)-cycloalkylcarbonyloxy,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₃-C₆)-cycloalkoxycarbonyloxy,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₃-C₆)-cycloalkylcarbonylamino,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonylamino,        -   (C₃-C₆)-cycloalkoxycarbonylamino,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonylamino and        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonylamino,        -   phenylcarbonyl,        -   phenyl-[(C₁-C₄)-alkyl]carbonyl,        -   phenyl-[(C₁-C₄)-alkoxy]carbonyl,        -   phenoxycarbonyl,        -   phenoxy-[(C₁-C₄)-alkyl]carbonyl,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonyl,        -   phenylcarbonyloxy,        -   phenyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   phenyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   phenoxycarbonyloxy,        -   phenoxy-[(C₁-C₄)-alkyl]carbonyloxy,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonyloxy,        -   phenylcarbonylamino,        -   phenyl-[(C₁-C₄)-alkyl]carbonylamino,        -   phenyl-[(C₁-C₄)-alkoxy]carbonylamino,        -   phenoxycarbonylamino,        -   phenoxy-[(C₁-C₄)-alkyl]carbonylamino,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonylamino,        -   where each of the 42 last-mentioned radicals is optionally            fused in the cyclic moiety with a carbocyclic or            heterocyclic ring, preferably a carbocyclic ring having 3 to            6 carbon atoms or a heterocyclic ring having 5 or 6 ring            atoms and 1 to 3 ring heteroatoms from the group consisting            of N, O and S, preferably benzo-fused, and unsubstituted at            the ring or at the polycyclic system or substituted by one            or more radicals from the group consisting of halogen,            (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,            (C₁-C₄)-haloalkoxy and nitro, and    -   (c) radicals of the formulae —SiR′₃, —O—SiR′₃,        (R′)₃Si—(C₁-C₄)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,        —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OH)₂, in which each of the        radicals R′ independently of the others represents H,        (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted        by one or more radicals from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-haloalkoxy and nitro or at two adjacent positions by a        (C₂-C₆)-alkylene bridge, and q represents an integer from 0 to        6, and    -   (d) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy, in        which each of the radicals R″ independently of the others        represents H or (C₁-C₄)-alkyl or together the radicals represent        a (C₁-C₆)-alkylene group and R′″ represents H or (C₁-C₄)-alkyl,    -   or-   R⁴ represents (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl,    (C₅-C₆)-cycloalkynyl or phenyl,    -   where each of the 4 last-mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        the radicals [subgroups (a′)-(e′)]    -   (a′) halogen, cyano, thio, nitro, hydroxy, carboxy,        (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,        (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy,        (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₆)-alkylthio,        (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio and radicals of the        formulae —NR*R**, where the radicals R* and R** are as defined        above or below,    -   (b′) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),        —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),        —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,        —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,        —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),        —P(═O)(OR^(c))(R^(D)), —P(═O)(OR^(c))(OR^(D)) and        —O—P(═O)(OR^(c))(OR^(D)), preferably a radical of the formula        —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(c) or        —O—C(═O)—O—R^(C), in particular a radical of the formula        —C(═O)—O—R^(C), —O—C(═O)—R^(c) or —O—C(═O)—O—R^(C),        -   where R*, R**, R^(C) and R^(D) are as defined below,        -   and preferably the radicals (b1′)        -   [(C₁-C₆)-alkoxy]carbonyl, [(C₁-C₆)-alkoxy]thiocarbonyl,            [(C₂-C₆)-alkenyloxy]carbonyl, [(C₂-C₆)-alkynyloxy]carbonyl,            [(C₁-C₆)-alkylthio]carbonyl, [(C₂-C₆)-alkenylthio]carbonyl,            [(C₂-C₆)-alkynylthio]carbonyl, (C₁-C₈)-alkanoyl,            [(C₂-C₆)-alkenyl]carbonyl, [(C₂-C₆)-alkynyl]carbonyl,            (C₁-C₄)-alkylimino, (C₁-C₄)-alkoxyimino,            [(C₁-C₆)-alkyl]carbonylamino,            [(C₂-C₆)-alkenyl]carbonylamino,            [(C₂-C₆)-alkynyl]carbonylamino,            [(C₁-C₆)-alkoxy]carbonylamino,            [(C₂-C₆)-alkenyloxy]carbonylamino,            [(C₂-C₆)-alkynyloxy]carbonylamino,            [(C₁-C₆)-alkylamino]carbonylamino,            [(C₁-C₄)-alkyl]carbonyloxy, [(C₂-C₄)-alkenyl]carbonyloxy,            [(C₂-C₄)-alkynyl]carbonyloxy, [(C₁-C₆)-alkoxy]carbonyloxy,            [(C₂-C₆)-alkenyloxy]carbonyloxy,            [(C₂-C₆)-alkynyloxy]carbonyloxy, (C₁-C₆)-alkylsulphinyl and            (C₁-C₆)-alkylsulphonyl,        -   where each of the 27 last-mentioned radicals is            unsubstituted or substituted by one or more radicals from            the group consisting of halogen, NO₂, (C₁-C₄)-alkoxy and            optionally substituted phenyl, and preferably the radicals            (b2′)        -   (C₃-C₆)-cycloalkylcarbonyl,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyl,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyl,        -   (C₃-C₆)-cycloalkoxycarbonyl,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyl,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyl,        -   (C₃-C₆)-cycloalkylcarbonyloxy,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₃-C₆)-cycloalkoxycarbonyloxy,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₃-C₆)-cycloalkylcarbonylamino,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonylamino,        -   (C₃-C₆)-cycloalkoxycarbonylamino,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonylamino and        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonylamino,        -   phenylcarbonyl,        -   phenyl-[(C₁-C₄)-alkyl]carbonyl,        -   phenyl-[(C₁-C₄)-alkoxy]carbonyl,        -   phenoxycarbonyl,        -   phenoxy-[(C₁-C₄)-alkyl]carbonyl,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonyl,        -   phenylcarbonyloxy,        -   phenyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   phenyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   phenoxycarbonyloxy,        -   phenoxy-[(C₁-C₄)-alkyl]carbonyloxy,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonyloxy,        -   phenylcarbonylamino,        -   phenyl-[(C₁-C₄)-alkyl]carbonylamino,        -   phenyl-[(C₁-C₄)-alkoxy]carbonylamino,        -   phenoxycarbonylamino,        -   phenoxy-[(C₁-C₄)-alkyl]carbonylamino,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonylamino,        -   where each of the 42 last-mentioned radicals is optionally            fused in the cyclic moiety with a carbocyclic or            heterocyclic ring, preferably a carbocyclic ring having 3 to            6 carbon atoms or a heterocyclic ring having 5 or 6 ring            atoms and 1 to 3 ring heteroatoms from the group consisting            of N, O and S, preferably benzo-fused, and unsubstituted at            the ring or at the polycyclic system or substituted by one            or more radicals from the group consisting of halogen,            (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,            (C₁-C₄)-haloalkoxy and nitro, and    -   (c′) radicals of the formulae —SiR′₃, —O—SiR′₃,        (R′)₃Si—(C₁-C₆)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,        —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OH)₂, in which each of the        radicals R′ independently of the others represents H,        (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted        by one or more radicals from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-haloalkoxy and nitro or at two adjacent positions by a        (C₂-C₆)-alkylene bridge, and q represents an integer from 0 to        6, and    -   (d′) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy, in        which each of the radicals R″ independently of the others is H        or (C₁-C₄)-alkyl or together the radicals are a (C₁-C₆)-alkylene        group and R′″ is H or (C₁-C₄)-alkyl, and    -   (e′) a radical of the formula Het⁷ which is unsubstituted or        substituted by one or more identical or different radicals        R^(B),    -   or-   R⁴ represents a polycyclic radical based on (C₃-C₆)-cycloalkyl,    (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl or phenyl, where the base    ring is fused with a carbocyclic or heterocyclic ring, preferably a    5- or 6-membered ring having 0 or 1 to 3 ring heteroatoms from the    group consisting of N, O and S, preferably benzo-fused, and where    the base ring or the polycyclic system is unsubstituted or    substituted by one or more identical or different radicals R^(B),    preferably unsubstituted or substituted by one or more radicals from    the group consisting of halogen, cyano, nitro, hydroxy, carboxy,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy,    (C₂-C₄)-alkynyloxy, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,    (C₂-C₄)-alkenylthio, (C₂-C₄)-alkynylthio, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, [(C₁-C₄)-alkoxy]carbonyl,    [(C₁-C₄)-haloalkoxy]carbonyl and oxo,    -   or-   R⁴ represents a heterocyclic radical Het⁷ which is unsubstituted in    the ring or in the polycyclic system or substituted by one or more    identical or different radicals R^(B), preferably unsubstituted or    substituted by one or more radicals from the group consisting of    halogen, cyano, thio, nitro, hydroxy, carboxy, (C₁-C₄)-alkyl,    (C₁-C6)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,    (C₁-C₆)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₄)-alkynyloxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₄)-alkylthio, (C₂-C₄)-alkenylthio, (C₂-C₄)-alkynylthio,    (C₃-C₄)-cycloalkyl, (C₃-C₆)-cycloalkoxy, [(C₁-C₄)-alkoxy]carbonyl,    [(C₁-C₆)-haloalkoxy]carbonyl and oxo,    where Het⁷, R*, R**, R^(A), R^(B), R^(C), R^(D), R^(aa), R^(bb) and    R^(cc) have the meanings already mentioned above, preferably-   Het⁷ in each case independently of the others is a saturated,    partially unsaturated or heteroaromatic monocyclic heterocyclyl    radical having 3 to 9 ring atoms, preferably having 5 or 6 ring    atoms, or a 9- or 10-membered bicyclic heterocycle which contains 1,    2, 3 or 4 heteroatoms selected from the group consisting of O, N and    S, preferably a 5- or 6-membered heterocycle having 1 to 3 ring    heteroatoms from the group consisting of N, O and S which is    optionally also fused to a carbocyclic or heterocyclic ring,    preferably a carbocyclic ring having 3 to 6 carbon atoms or a    heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring    heteroatoms from the group consisting of N, O and S, preferably    optionally benzo-fused,-   R*, R** independently of one another (i.e. also of other groups    NR*R**) each represent H, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,    [(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,    [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, phenyl-(C₁-C₄)-alkyl,    where each of the 4 last-mentioned radicals is optionally    substituted in the cycle by one or more identical or different    radicals R^(bb), or preferably    -   H, (C₁-C₄)-alkyl, allyl, propargyl,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, formyl, acetyl, n-propanoyl,        isopropanoyl, trifluoroacetyl, trichloroacetyl, methoxycarbonyl,        ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, sec-,        t-Butoxycarbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl, cyclopropyl,        cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, phenyl,        benzyl, 1- or 2-phenylethyl,-   R* and R** together with the nitrogen atom represent a preferably    saturated 5- to 6-membered heterocycle which, in addition to the    nitrogen atom, may contain one or two further ring heteroatoms from    the group consisting of N, O and S and which may be unsubstituted or    substituted by one or more radicals from the group consisting of    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, preferably a 1-piperidine,    1-piperazine, 1-pyrrolidine, 1-pyrazolidine, 1-piperazolidine or    1-morpholine radical,-   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy,-   R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, cyano-(C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkyl,    nitro-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,    (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₄)-alkynyloxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkylsulphonyl, a radical of the    formula R^(aa)—C(═O)— or R^(aa)—C(═O)—(C₁-C₆)-alkyl, where the    radicals R^(aa) are defined below, —NR*R**, where R* and R** are    defined below, cyclopropyl, cyclopropylmethyl, phenyl, benzyl, 1- or    2-phenylethyl, phenoxy, 2-phenoxyethyl or a 5- or 6-membered    monocyclic or 9- or 10-membered bicyclic heterocycle which contains    1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N    and S, where each of the 9 last-mentioned radicals is optionally    substituted in the cyclic moiety by one or more identical or    different radicals R^(bb),-   R^(C), R^(D) are each independently of one another (also    independently of radicals R^(C), R^(D) in other groups)    -   hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,        -   where each of the 3 last-mentioned radicals is unsubstituted            or substituted by one or more radicals from the group            consisting of halogen, cyano, nitro, hydroxy,            (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₄)-alkynyloxy,            (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,            (C₁-C₄)-alkylthio, (C₁-C₆)-alkylsulphonyl and            (C₁-C₈)-haloalkylsulphonyl,    -   or    -   (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl,        phenyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl-(C₁-C₄)-alkyl,        phenoxy-(C₁-C₄)-alkyl or phenylamino-(C₁-C₆)-alkyl, radicals        Het⁷, Het⁷-(C₁-C₆)-alkyl, Het⁷-O—(C₁-C₆)-Alkyl, where Het⁷ has        the meaning mentioned,        -   where each of the 12 last-mentioned radicals is            unsubstituted in the acyclic moiety or substituted by one or            more identical or different radicals R^(A) and is            unsubstituted in the cyclic moiety or substituted by one or            more identical or different radicals R^(B),-   R^(aa) independently of one another each represent hydrogen, OH,    (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,    (C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyloxy, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkoxy,    —NR*R*, where R* and R** are as defined above, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₄)-alkyl,    phenyl-(C₁-C₄)-alkoxy, phenoxy, phenoxy-(C₁-C₄)-alkyl,    phenoxy-(C₁-C₄)-alkoxy, phenylamino, phenylamino-(C₁-C₄)-alkyl,    phenylamino-(C₁-C₄)-alkoxy or 5- or 6-membered monocyclic or 9- or    10-membered bicyclic heterocycle which is optionally attached via a    (C₁-C₄)-alkylene group or a (C₁-C₄)-alkoxy group and contains 1, 2,    3 or 4 heteroatoms selected from the group consisting of O, N and S,    where each of the 14 last-mentioned radicals is optionally    substituted in the cyclic moiety by one or more identical or    different radicals R^(cc),-   R^(bb) independently of one another each represent halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or    (C₁-C₄)-haloalkoxy, preferably halogen, methyl, CF₃, CCl₃, methoxy,    ethoxy, OCH₂F, OCF₂H or OCF₃ and-   R^(cc) independently of one another each represent halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or    (C₁-C₄)-haloalkoxy, preferably halogen, methyl, CF₃, CCl₃, methoxy,    ethoxy, OCH₂F, OCF₂H or OCF₃.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R⁴ represents H, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    -   where each of the 3 last-mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, alkylsulphinyl,        alkylsulphonyl, (C₃-C₆)-cycloalkyl which is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen and (C₁-C₄)-alkyl, and    -   phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl,        where the phenyl ring in the 5 last-mentioned radicals is in        each case unsubstituted or substituted by one or more radicals        from the group consisting of halogen, (C₁-C₄)-alkyl,        (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl, and    -   a radical Het⁷, preferably a saturated or partially unsaturated        monocyclic heterocyclyl radical which has 5 or 6 ring atoms and        contains 1, 2 or 3 heteroatoms selected from the group        consisting of O, N and S and is unsubstituted or substituted by        one or more radicals selected from the group consisting of        halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl,    -   or-   R⁴ represents (C₃-C₆)-cycloalkyl which is unsubstituted or    substituted by one or more radials from the group consisting of    (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl,    -   or-   R⁴ represents phenyl which is unsubstituted or substituted by one or    more radials from the group consisting of halogen, (C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl.

Particular preference is here also given to compounds (I), preferably ofthe formula (Ia), or salts thereof in which

-   R⁴ represents H, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or (C₂-C₄)-alkynyl,    -   where each of the 3 last-mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, cyclopropyl,        cyclobutyl, where each of the two last-mentioned radicals is        unsubstituted or substituted by one or more radicals from the        group consisting of halogen and (C₁-C₄)-alkyl, and phenyl,        phenylthio (=phenylsulphanyl), phenylsulphinyl, phenylsulphonyl,        where each of the 4 last-mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl.

More preferably

-   R⁴ also represents a polycyclic radical based on (C₃-C₉)-cycloalkyl,    (C₅-C₉)-cycloalkenyl, (C₅-C₉)-cycloalkynyl or phenyl, where the base    ring is condensed, preferably benzo-fused, with a carbocyclic or    heterocyclic ring, preferably a 5- or 6-membered ring having 0 or 1    to 3 ring heteroatoms from the group consisting of N, O and S, and    where the base ring or the polycyclic system is unsubstituted or    substituted by one or more radicals from the group consisting of    halogen, cyano, nitro, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₄)-alkylthio, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkoxy,    [(C₁-C₄)-alkoxy]carbonyl and [(C₁-C₄)-haloalkoxy]carbonyl.

Preference is also given to compounds (I), preferably of the formula(Ia), or salts thereof in which

-   R⁴ represents a saturated, partially unsaturated or heteroaromatic    heterocyclyl radical which has 3 to 9 ring atoms, preferably 5 or 6    ring atoms, which has 1 to 4 heteroatoms, preferably 1 to 3 ring    heteroatoms from the group consisting of N, O and S and which is    unsubstituted or substituted by one or more identical or different    radicals from the group consisting of halogen, cyano, thio, nitro,    hydroxy, (C1-C₆)-alkyl, (C₁-C6)-haloalkyl,    (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy,    (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,    (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,    (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, [(C₁-C₈)-alkoxy]carbonyl,    [(C₁-C₆)-haloalkoxy]carbonyl and oxo.

Preference is also given to compounds (I), preferably of the formula(Ia), or salts thereof in which

-   R⁴ represents a radical of the formula SiR^(a)R^(b)R^(c),    —NR^(a)R^(b) or —N═CR^(c)R^(d), preferably of the formula    —NR^(a)R^(b) or —N═CR^(c)R^(d),    -   where in the 5 last-mentioned formulae each of the radicals        R^(a), R^(b), R^(c) and R^(d) independently of the others        represents hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,        (C₂-C₄)-alkynyl, benzyl, substituted benzyl, phenyl or        substituted phenyl, but where SiH₃ for SiR^(a)R^(b)R^(c) is        excluded, or R^(a) and R^(b) together with the nitrogen atom        represent a 3- to 8-membered heterocycle which, in addition to        the nitrogen atom, may contain one or two further ring        heteroatoms from the group consisting of N, O and S and which is        unsubstituted or substituted by one or more radicals from the        group consisting of (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, or        R^(c) and R^(d) together with the carbon atom represent a 3- to        8-membered carbocyclic radical or heterocyclic radical which may        contain 1 to 3 ring heteroatoms from the group consisting of N,        O and S, where the carbocyclic or heterocyclic radical is        unsubstituted or substituted by one or more radicals from the        group consisting of (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl.

Particular preference is also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R⁴ represents H, methyl, ethyl, n-propyl, i-propyl, n-butyl,    s-butyl, i-butyl, t-butyl, allyl, ethynyl, propargyl    (prop-2-yn-1-yl), prop-1-yn-1-yl, but-2-yn-1-yl, but-3-yn-1-yl,    2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl,    3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl,    methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,    but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl,    3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl,    1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or    (Z)-pent-3-en-2-yl,    -   phenyl, 2-carboxyphenyl, 2-chlorophenyl, 3-chlorophenyl,        4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,        3-methoxyphenyl, 4-methoxyphenyl, 2-methoxyphenyl,        3-methoxyphenyl, 4-methoxyphenyl, benzyl, 2-fluorobenzyl,        2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl,        2,3-difluorobenzyl, 2,4-difluorobenzyl, 2,5-difluorobenzyl,        2,6-difluorobenzyl, 3,4-difluorobenzyl, 3,5-difluorobenzyl,        2-phenylethyl, 1-phenylethyl, (4-chlorophenyl)methyl [i.e.        ═CH₂(4-Cl-Ph)=4-chlorobenzyl], (4-fluorophenyl)methyl [d. h.        ═CH₂(4-F-Ph)], (4-methoxyphenyl)methyl [i.e. ═CH₂(4-OMe-Ph)],        2-phenoxyethyl, 2-phenylthioethyl [=2-(phenylsulphanyl)ethyl],        2-phenylsulphinylethyl, 2-phenylsulphonylethyl, trifluoromethyl,        difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl,        chloromethyl,    -   methoxymethyl, 2-methoxyethyl, 2,2,2-trifluoroethyl,        1,1,1-trifluoroprop-2-yl, 2,2-difluoroethyl,        1,3-difluoroprop-2-yl, 2,3-dimethoxypropyl,        2,3-dimethoxyprop-2-yl, 2,2-dimethoxyeth-2-yl,        2-(2,2,2-trifluoroethoxy)ethyl, 2-fluoroethyl, 2-chloroethyl,        2-bromoethyl, 2-iodoethyl, 2,2,3,3,3-pentafluoropropyl,        1-hydroxyprop-2-yl, 2-hydroxyprop-2-yl, 2-hydroxyprop-1-yl,        3-hydroxypropyl, 3-hydroxyprop-2-yl,    -   (2-methoxyethoxy)methyl; 2-(2-methoxyethoxy)ethyl;        (2-ethoxyethoxy)methyl; 2-(2-ethoxyethoxy)ethyl,    -   (acetoxy)methyl, (propanoyloxy)methyl,        (2-methylpropanoyloxy)methyl, (2,2-dimethylpropanoyloxy)methyl,        1-(acetoxy)ethyl, 2-(acetoxy)ethyl, 2-(propanoyloxy)ethyl,        1-(propanoyloxy)ethyl, 1-(2-methylpropanoyloxy)eth-1-yl,        2-(2-methylpropanoyloxy)eth-1-yl,        2-(2,2-dimethylpropanoyloxy)ethyl [i.e.        1-(t-butylcarbonyloxy)ethyl], 2-(2,2-dimethylpropanoyloxy)ethyl;    -   1-(2,2-dimethylpropanoyloxy)-2-methylprop-1-yl,        1-(t-butylcarbonyloxy)-2-methylprop-1-yl,    -   (methoxycarbonyl)methyl, (ethoxycarbonyl)methyl,        (n-propoxycarbonyl)methyl, (1-propoxycarbonyl)methyl,        (n-butoxycarbonyl)methyl, (s-butoxycarbonyl)methyl,        (1-butoxycarbonyl)methyl, (t-butoxycarbonyl)methyl,        1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl,        1-(ethoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl,        1-(n-propoxycarbonyl)ethyl, 2-(n-propoxycarbonyl)ethyl,        1-(1-propoxycarbonyl)ethyl, 2-(1-propoxycarbonyl)ethyl,        1-(n-butoxycarbonyl)ethyl, 2-(n-butoxycarbonyl)ethyl,        1-(s-butoxycarbonyl)ethyl, 2-(s-butoxycarbonyl)ethyl,        1-(1-butoxycarbonyl)ethyl, 2-(1-butoxycarbonyl)ethyl,        1-(t-butoxycarbonyl)ethyl, 2-(t-butoxycarbonyl)ethyl,    -   (methoxycarbonyloxy)methyl, (ethoxycarbonyloxy)methyl,        (n-propoxycarbonyloxy)methyl, (1-propoxycarbonyloxy)methyl,        (n-butoxycarbonyloxy)methyl, (s-butoxycarbonyloxy)methyl,        (1-butoxycarbonyloxy)methyl, (t-butoxycarbonyloxy)methyl,        1-(methoxycarbonyloxy)ethyl, 2-(methoxycarbonyloxy)ethyl,        1-(ethoxycarbonyloxy)ethyl, 2-(ethoxycarbonyloxy)ethyl,        1-(n-propoxycarbonyloxy)ethyl, 2-(n-propoxycarbonyloxy)ethyl,        1-(1-propoxycarbonyloxy)ethyl, 2-(1-propoxycarbonyloxy)ethyl,        1-(n-butoxycarbonyloxy)ethyl, 2-(n-butoxycarbonyloxy)ethyl,        1-(s-butoxycarbonyloxy)ethyl, 2-(s-butoxycarbonyloxy)ethyl,        1-(1-butoxycarbonyloxy)ethyl, 2-(1-butoxycarbonyloxy)ethyl,        1-(t-butoxycarbonyloxy)ethyl, 2-(t-butoxycarbonyloxy)ethyl,        (cyclohexoxycarbonyloxy)methyl,        1-(cyclohexoxycarbonyloxy)eth-1-yl,        2-(cyclohexoxycarbonyloxy)eth-1-yl,    -   (acetyl)methyl, 1-(acetyl)ethyl, 2-(acetyl)ethyl,        1-(acetyl)propyl, 2-(acetyl)propyl, 3-(acetyl)propyl,        (propanoyl)methyl, 1-(propanoyl)ethyl, 2-(propanoyl)ethyl,        1-(propanoyl)propyl, 2-(propanoyl)propyl, 3-(propanoyl)propyl,        1-(propanoyl)-2-methylpropyl,    -   2-ethylthioethyl [=2-(ethylsulphanyl)ethyl],        2-(ethylsulphinyl)ethyl, 2-(ethylsulphonyl)ethyl,    -   2-(ethylideneaminooxy)ethyl, 2-(prop-2-ylideneaminooxy)ethyl,        2-(but-2-ylideneaminooxy)ethyl, 2-(pent-3-ylideneaminooxy)ethyl,    -   (N,N-dimethylamino)methyl, 2-(N,N-dimethylamino)eth-1-yl,        1-(N,N-dimethylamino)eth-1-yl, 2-(N,N-diethylamino)eth-1-yl,        1-(N,N-diethylamino)eth-1-yl, (N,N-diethylamino)methyl,    -   (N,N-dimethylaminocarbonyl)methyl,        1-(N,N-dimethylaminocarbonyl)ethyl,        2-(N,N-dimethylaminocarbonyl)ethyl,        (N,N-diethylaminocarbonyl)methyl,        1-(N,N-diethylaminocarbonyl)ethyl,        2-(N,N-diethylaminocarbonyl)ethyl, 1-(dimethylamino)prop-2-yl        [i.e. 2-(dimethylamino)-1-methylethyl],        1-(diethylamino)prop-2-yl,    -   trimethylsilylmethyl, 1-(trimethylsilyl)ethyl,        2-(trimethylsilyl)ethyl, triethylsilylmethyl,        1-(triethylsilyl)ethyl, 2-(triethylsilyl)ethyl,    -   cyclopropyl, cyclopropylmethyl, 1-cyclopropylethyl,        2-cyclopropylethyl, (1-methylcyclopropyl)methyl,        1-(1-methylcyclopropyl)ethyl, 2-(1-methylcyclopropyl)ethyl,        (2,2-dichlorcyclopropyl)methyl, 1-(2,2-dichlorcyclopropyl)ethyl,        2-(2,2-dichlorcyclopropyl)ethyl,        (2,2-dimethylcyclopropyl)methyl,        1-(2,2-dimethylcyclopropyl)ethyl,        2-(2,2-dimethylcyclopropyl)ethyl, cyclobutylmethyl,        cyclopentylmethyl, cyclohexylmethyl or    -   pyrid-2-yl, pyrid-3-yl, pyrid-4-yl, 2-chloropyrid-3-yl,        3-chloropyrid-2-yl, thien-2-yl, thien-3-yl, 2-chlorothien-3-yl,        3-chlorothien-2-yl, 4-chlorothien-2-yl, thietan-3-yl,    -   (1-ethyl-5-methyl-1H-pyrazol-4-yl)methyl,        1-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethyl,        2-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethyl,    -   (1-ethyl-3-methyl-1H-pyrazol-4-yl)methyl,        1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)ethyl,        2-(1-ethyl-3-methyl-1H-pyrazol-4-yl)ethyl,    -   tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,        tetrahydrofuran-2-ylmethyl, tetrahydrofuran-3-ylmethyl,        (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl;    -   oxetan-3-yl, (oxetan-3-yl)methyl, (oxetan-2-yl)methyl,        (1,3-dioxolan-2-yl)methyl, (1,3-dioxolan-4-yl)methyl,        5-methyl-2-oxo-1,3-dioxolan-4-yl)methyl, (morpholin-4-yl)methyl;        1-(morpholin-4-yl)ethyl, 2-(morpholin-4-yl)ethyl,        2,3-dihydro-1H-inden-2-yl, dihydro-1H-inden-3-yl,        dihydro-1H-inden-4-yl, dihydro-1H-inden-5-yl, 1H-inden-2-yl,        1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl or        1H-inden-7-yl.

Here, very particular preference is given to compounds (I), preferablyof the formula (Ia), and salts thereof in which

-   R⁴ represents H, methyl, ethyl, n-propyl, isopropyl, n-butyl,    s-butyl, isobutyl, t-butyl, phenyl, benzyl, CH₂(4-Cl-Ph), i.e.    (4-chlorophenyl)methyl, CH₂(4-F-Ph), i.e. (4-fluorophenyl)methyl,    CH₂(4-OMe-Ph), i.e. (4-methoxyphenyl)methyl, 2-fluorobenzyl,    2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2,3-difluorobenzyl,    2,4-difluorobenzyl, 2,5-difluorobenzyl, 2,6-difluorobenzyl,    3,4-difluorobenzyl, 3,5-difluorobenzyl, 2-phenoxyethyl,    2-ethylthioethyl, 2-ethylsulphinylethyl, 2-ethylsulphonylethyl,    2-phenylthioethyl, 2-phenylsulphinylethyl, 2-phenylsulphonylethyl,    methoxymethyl, 2-methoxyethyl, tetrahydrofuran-2-ylmethyl,    2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl,    thietan-3-yl, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl,    2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl,    cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl,    (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl,    tetrahydrofuran-2-ylmethyl, allyl, ethynyl, propargyl    (=prop-2-yn-1-yl), prop-1-yn-1-yl, 2-chloroprop-2-en-1-yl,    3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl,    3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl,    2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl,    but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl,    3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl,    (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl,    cyclopentylmethyl, cyclohexylmethyl or    1-ethyl-5-methyl-1H-pyrazol-4-methyl, i.e.    (1-ethyl-5-methyl-1H-pyrazol-4-yl)methyl.

Here, very particular preference is given to compounds (I), preferablyof the formula (Ia), and salts thereof in which

-   R⁴ represents H, methyl, ethyl, n-butyl, s-butyl, isobutyl, t-butyl,    allyl and propargyl, in particular methyl or ethyl.

The invention also includes all tautomers, such as keto and enoltautomers, and their mixtures and salts, if appropriate functionalgroups are present.

The present invention also provides processes for preparing thecompounds of the general formula (I) or (Ia) and/or their salts. Thisincludes processes which can be carried out analogously to knownmethods.

To prepare the compounds (I) according to the invention, it is possibleto use initially the corresponding diastereomer mixtures in the form oftheir racemic mixtures. The preparation of the diastereomer mixtures ofthe cyanobutyrates is known in principle; see, for example, EP-A 5341,EP-A 266725, EP-A270 830, JP 04/297454, JP 04/297455, JP 05/058979, WO2011/003776, WO 2011/003775, WO 2011/042378, WO 2011/073143, WO2011/098417.

Analogously to the synthesis routes described in the publications cited,the compounds can be prepared by standard processes of organicchemistry.

Diastereomer mixtures of the compounds of the formula (I) comprising thecompound (I) to be prepared are obtained, for example, characterized inthat

(a) compounds of the formula (II)(“cyanomethylpyridines”/“pyridylacetonitriles”)

-   -   are reacted with compounds of the formula (III) (cinnamic acid        derivatives) or salts thereof

-   -   to give compounds of the formula (I) (diastereomers/racemic)

-   -   where R¹, R², R³, R⁴, m and n in the compounds (II) and (III)        are as defined in the respective compound of the formula (I) to        be prepared.

In the process mentioned above and in the processes below, in some casessolvents are employed. In this context, “inert solvents” refers in eachcase to solvents which are inert under the particular reactionconditions, but which do not have to be inert under all reactionconditions.

The process described in each case can be carried out in apparatusescustomary in the laboratory, in pilot plants and in plants for preparingcommercial amounts and industrial processes, or alternatively also in amicrowave oven.

The starting materials (III) required for preparing the compounds (I)are known from the literature cited above or can be prepared analogouslyto the literature cited.

The starting materials (II) required for preparing the compounds (I) arecommercially available, described in the literature or can be preparedanalogously to processes described in the literature.

The reaction according to variant (a) can be carried out, for example,according to methods and under conditions like those known for Michaeladditions. The reaction is carried out, for example, at temperatures offrom −100° C. to 150° C., preferably from −78° C. to 100° C., in anorganic or inorganic solvent, generally in the presence of a base or acatalyst or both [cf. J. Chem. Soc. (1945), p. 438].

Suitable solvents are, for example, organic solvents such as:

-   -   aliphatic hydrocarbons such as pentane, hexane, cyclohexane or        petroleum ether;    -   aromatic hydrocarbons such as toluene, o-, m- or p-xylene,    -   halogenated hydrocarbons such as methylene chloride, chloroform        or chlorobenzene,    -   ethers, such as diethyl ether, diisopropyl ether, tert-butyl        methyl ether, dioxane, anisole and tetrahydrofuran (THF),    -   nitriles such as acetonitrile or propionitrile,    -   ketones such as acetone, methyl ethyl ketone, diethyl ketone and        tert-butyl methyl ketone,    -   alcohols such as methanol, ethanol, n-propanol, isopropanol,        n-butanol and tert-butanol, and also    -   dimethyl sulphoxide, dimethylformamide, dimethylacetamide,        sulpholane,    -   mixtures of the organic solvents mentioned.

In individual cases, it is also appropriate to use inorganic solventssuch as water or mixtures of organic solvents with water.

Preferred solvents are THF, toluene and methanol, and mixtures thereofwith other organic solvents.

The reaction by preparation variant (a) is preferably carried out in thepresence of a base, for example from the group consisting of theinorganic compounds such as the alkali metal and alkaline earth metalhydroxides, for example lithium hydroxide, sodium hydroxide, potassiumhydroxide or calcium hydroxide, the alkali metal and alkaline earthmetal oxides, for example lithium oxide, sodium oxide, calcium oxide ormagnesium oxide, the alkali metal and alkaline earth metal hydrides, forexample lithium hydride, sodium hydride, potassium hydride or calciumhydride, the alkali metal amides, for example lithium amide, sodiumamide or potassium amide, the alkali metal and alkaline earth metalcarbonates, for example lithium carbonate, potassium carbonate orcalcium carbonate, the alkali metal bicarbonates, for example sodiumbicarbonate, or the organometallic compounds such as, preferably, thealkali metal alkyls, for example methyllithium, butyllithium orphenyllithium, the alkylmagnesium halides, for example methylmagnesiumchloride, or the alkali metal and alkaline earth metal alkoxides, forexample sodium methoxide, sodium ethoxide, potassium ethoxide, potassiumtert-butoxide or dimethoxymagnesium.

The bases used can also be organic bases, for example from the groupconsisting of the tertiary aliphatic amines, for example trimethylamine,triethylamine, tributylamine, diisopropylethylamine orN-methylpiperidine, or the aromatic tertiary amines, for examplepyridine or substituted pyridines such as collidine, lutidine or4-dimethylaminopyridine, or the bicyclic amines such as7-methyl-1,5,7-triazabicyclo[4.4.0]-dec-5-ene or1,8-diazabicyclo[5.4.0]undec-7ene (DBU). Preferred bases are, forexample, potassium tert-butoxide, lithium bis(trimethylsilyl)amide, DBUor 7-methyl-1,5,7-triazabicyclo[4.4.0]-dec-5-ene.

The amount of base may generally be varied within wide limits. Forexample, it may be expedient to employ the base in catalytic amounts, insubstoichiometric amounts, in equimolar amounts or in excess. Apreferably liquid organic base may optionally also be used as solvent.

Suitable catalysts for the Michael addition according to variant (a) areacidic catalysts, for example from the group consisting of the inorganicacids, for example Broensted acids, such as hydrofluoric acid,hydrochloric acid, hydrobromic acid, sulphuric acid or perchloric acid,or Lewis acids, such as boron trifluoride, aluminium trichloride,iron(III) chloride, tin(IV) chloride, titanium(IV) chloride,scandium(III) triflate or zinc(II) chloride, and also organic acids, forexample formic acid, acetic acid, propionic acid, oxalic acid,toluenesulphonic acid, benzenesulphonic acid, camphorsulphonic acid,citric acid or trifluoroacetic acid.

The amount of acidic catalyst may generally be varied within widelimits. For example, it may be expedient to employ the acid in catalyticamounts, in substoichiometric amounts, in equimolar amounts or inexcess. A preferably liquid acid may optionally also be used as solvent.

Variant (a1) for the preparation of intermediates of the formula (II):

Compounds of the formula (II) and salts thereof in which R¹, R³ and mare defined as in the respective compound of the formula (I) to beprepared are also obtained, for example, according to process [variant(a1)], characterized in that a pyridinecarboxylic acid of the formula(IV) or its ester of the formula (V),

where the radical R in the formula (V) represents a hydrocarbon radical,preferably (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl or(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, in particular methyl or ethyl, is reducedto give the compound of the formula (VI) (=reduction at the acid orester group),

and the compound (VI) is converted into the compound (VII),

where X represents a leaving group, for example halogen, such aschlorine, bromine or iodine, obtained by a halogenation reaction suchas, for example, substitution by halide, or sulphonates of the formula—O—SO₂—R(R═(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, phenyl, which is optionallysubstituted, for example by halogen, nitro or alkyl), for examplemesylate (R=methyl), triflate (R=CF₃), tosylate (R=p-tolyl), bromylate(R=p-bromophenyl), nosylate (R=p-nitrophenyl), obtained byesterification of an appropriate sulphonyl chloride with compounds ofthe formula (VI),and the compound (VII) is converted by substitution with cyanide intothe compound (II),

where R¹, R³ and m in the formulae (IV), (V), (VI) and (VII) are asdefined in formula (II) or formula (I).

The individual synthesis steps according to variant (a1) are known inprinciple to the person skilled in the art and described, for example,in Acta Pharm. Suecica 1972, 9, 411-418; J. Org. Chem. 1999, 64 (23),8576-8581; Synthesis 1998, 9, 1335-1338; J. Med. Chem. 2000, 43 (18)3386-3399; U.S. Pat. No. 5,225,423 (Shell Research Limited 1993), U.S.Pat. No. 4,966,902 (Hoechst AG, 1990); WO2007/045989 (Pfizer Limited,2007); US2004/242572 (Boehringer Ingelheim International GmbH, 2004) andthe literature cited therein.

Diastereomer mixtures or racemic diastereomers of the compounds of theformula (I) can be obtained according to variant (b) bytransesterification, characterized in that

(b) compounds of the formula (I*)

-   -   in which R is a radical from the group consisting of the        radicals possible for R⁴′ but different from the radical R⁴ in        the compound (I) to be prepared, is reacted with a compound of        the formula R⁴—OH in which R⁴ is defined as in formula (I), to        give compound (I), where R¹, R², R³, m and n in the compound        (I*) are as defined in the compound of the formula (I) to be        prepared in each case.

In a particular embodiment, according to variant (b1) it is alsopossible to obtain, as compounds (I), stereochemically enrichedcompounds of the formula (Ia), characterized in that (b1)stereochemically enriched compounds of the formula (Ia*), whichcorrespond stereochemically [i.e. are at least as enriched as in thedesired compound (Ia)]

-   -   in which R is a radical from the group consisting of the        radicals possible for R⁴, but different from the radical R⁴ in        the compound (Ia) to be prepared, is reacted with a compound of        the formula R⁴—OH in which R⁴ is defined as in the compound of        the formula (Ia) to be prepared.

The transesterifications (b) and (b1) can be carried out, for example,using a suitable alcohol R⁴—OH in the presence of a catalyst, optionallyin the presence of an aprotic solvent. Furthermore, in general, thoseconditions are advantageous where the chemical equilibrium is shifted tothe side of the desired product, for example using a large excess of thealcohol R⁴—OH under virtually anhydrous conditions, for example in thepresence of a molecular sieve.

The reactions (transesterifications) can generally be carried out attemperatures of from 0° C. to 180° C., preferably from 20° C. to 100°C., in the presence of a Lewis or Broenstedt acid or an enzyme [cf. J.Org. Chem. 2002, 67, 431].

Suitable solvents are, for example, organic aprotic solvents such as:

-   -   aliphatic hydrocarbons such as pentane, hexane, cyclohexane or        petroleum ether;    -   aromatic hydrocarbons such as toluene, o-, m- or p-xylene,    -   halogenated hydrocarbons such as methylene chloride        (dichloromethane), chloroform or chlorobenzene,    -   ethers, such as diethyl ether, diisopropyl ether, tert-butyl        methyl ether, dioxane, anisole or tetrahydrofuran (THF),    -   nitriles such as acetonitrile or propionitrile,    -   ketones such as acetone, methyl ethyl ketone, diethyl ketone and        tert-butyl methyl ketone,    -   dimethyl sulphoxide, dimethylformamide, dimethylacetamide or        sulpholane or    -   mixtures of the organic solvents mentioned.

The preferred solvent is the alcohol R⁴—OH, which is at the same timeused as reaction partner for the transesterification, optionally incombination with one of the aprotic organic solvents mentioned.

Alternatively, it is also possible to obtain the desired ester fromanother ester in two steps by acidic or basic hydrolysis of the otheresters to the free acid, i.e. to compounds (1*) or (Ia*), in which R isin each case H, and subsequent esterification with an alcohol R⁴—OH.

Variants (c) and (c1):

The preparation of diastereomer mixtures or racemic diastereomers of theformula (I) according to variant (c) or optically active compounds (Ia)according to variant (c1) is therefore characterized in that a compoundof the abovementioned formula (I*) or the formula (Ia*) in which theradicals R are each hydrogen (free carboxylic acids) is esterified withan alcohol of the formula R⁴—OH by customary methods, if appropriatecombined with a previous preparation (c-1) or (c1-1) of the free acidfrom another ester of the formula (I*) or the formula (Ia*) in which theradicals R are each not hydrogen.

The esterification from the free acid of the formula (I*)/R═H or(Ia*)/R═H can be carried out, for example, analogously to customarymethods, for example at temperatures of from 0° C. to 120° C.,preferably from 20° C. to 50° C., optionally in the presence of acatalyst, in a substantially anhydrous medium or under conditions wherethe water including the water formed during the esterification is boundor otherwise removed. Suitable catalysts are anhydrous acids and bases,preferably organic acids or bases; see handbooks for chemical processesfor esterifying carboxylic acids; see also, for example, J. Am. Chem.Soc. 2007, 129 (43), 13321; J. Org. Chem. 1984, 49 (22), 4287.

Suitable solvents for the esterification are the aprotic organicsolvents mentioned above for process variants (b) and (b1), includingthe alcohol R⁴—OH which is at the same time used as a reaction partnerfor the esterification, optionally in combination with one of theaprotic organic solvents mentioned.

Suitable catalysts for the esterification are the bases or acidic orbasic catalysts mentioned for mentioned process variant (a) (Michaeladdition), in anhydrous form or with a water content which is as low aspossible. Preferred catalysts are the bases lithium hydroxide, potassiumcarbonate or organic amines such as pyridines, substituted pyridines andDBU.

Any hydrolysis carried out before the esterification [process variants(c-1) and (c1-1)] of other esters of the formula (I*) or the formula(Ia*), where R is in each case not H, can be carried out analogously tocustomary methods, for example at temperatures of from 0° C. to 120° C.,preferably from 20° C. to 50° C., if appropriate in the presence of acatalyst, in a water-containing medium/solvent; see handbooks onchemical processes for hydrolysing carboxylic esters; see also, forexample, J. Am. Chem. Soc. 2007, 129 (43), 13321; J. Org. Chem. 1984, 49(22), 4287.

A suitable solvent for the hydrolysis [process variants (c-1) and(c1-1)] is water or a water-containing organic solvent, for example theorganic solvent mentioned based on process variant (a) mentioned(Michael addition), preferably water or polar organic solventscontaining water, such as THF.

Suitable catalysts for the hydrolysis are the acids, bases or acidic orbasic catalysts mentioned for process variant (a) (Michael addition), ineach case containing water. Preferred catalysts are aqueous acids andbases, in particular bases such as lithium hydroxide, sodium hydroxide,potassium carbonate, pyridines, substituted pyridines and DBU in thepresence of organic solvents.

The catalysts for the esterification or the hydrolysis can generally beemployed in catalytic amounts. In general, it is also possible to userelatively large amounts including equimolar amounts or in molar excess.Frequently, a use as solvent is also possible.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separating the phases and, if appropriate,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of colourless orslightly brownish viscous oils which are purified or freed from volatilecomponents under reduced pressure and at moderately elevatedtemperature.

If the intermediates and end products are obtained as solids, thepurification can also be carried out by recrystallization or digestion.If individual compounds (I) or (Ia) cannot be obtained by the routesdescribed above, they can be prepared by derivatization of othercompounds (I) or (Ia).

To prepare the erythro compounds, threo compounds or optically activeerythro or threo compounds according to the invention, preferably thethreo compounds (Ia), from the diastereomer mixtures of the compounds(I), it is necessary to enrich the respective diastereomer, for examplethe threo isomer or the stereoisomer (enantiomer) erythro-1, erythro-2,threo-1 or threo-2, preferably threo-2, from the mixture of thestereoisomers in an appropriate manner. Accordingly, an expedientprocess comprises the initial isolation of the erythro-1 and erythro-2or threo isomers threo-1 and threo-2 from the diastereomer mixture ofthe compounds of the formula (I) which still comprises the otherisomers, and optionally the subsequent optical resolution with isolationor enrichment of the enantiomer from the mixture with the otherenantiomers.

The isolation of the diastereomers as a racemic mixture can be carriedout analogously to the customary separation and purification processesmentioned above (diastereomer separation).

Suitable for the subsequent preparation of compounds of the opticallyactive compounds (I), preferably for the formula (Ia), are methods foroptical resolution generally known to the person skilled in the art fromanalogous cases (cf. handbooks of stereochemistry), for examplefollowing processes for separating mixtures into diastereomers, forexample by physical processes, such as crystallization, chromatographicprocesses, in particular column chromatography and high-pressure liquidchromatography, distillation, if appropriate under reduced pressure,extraction and other processes, it is possible to separate remainingmixtures of enantiomers, generally by chromatographic separation onchiral solid phases. Suitable for preparative amounts or on anindustrial scale are processes such as the crystallization ofdiastereomeric salts which can be obtained from the diastereomermixtures using optically active acids and, if appropriate, provided thatacidic groups are present, using optically active bases.

Optically active acids which are suitable for optical resolution bycrystallization of diastereomeric salts are, for example,camphorsulphonic acid, camphoric acid, bromocamphorsulphonic acid,quinic acid, tartaric acid, dibenzoyltartaric acid and other analogousacids; suitable optically active bases are, for example, quinine,cinchonine, quinidine, brucine, 1-(S)- or 1-(R)-phenylethylamine andother analogous bases.

The crystallizations are then in most cases carried out in aqueous,alcoholic or aqueous-organic solvents, where the diastereomer which isless soluble precipitates first, if appropriate after seeding. Oneenantiomer of the compound of the formula (I) is then liberated from theprecipitated salt, or the other is liberated from the crystals, byacidification or using a base.

Accordingly, the invention also provides the process for preparing theoptically active compounds (I) [variant (d)], preferably (Ia),characterized in that

(d) an optical resolution is carried out with compounds (I), preferablythe erythro compounds or in particular the threo compounds of theformula (I), and the desired enantiomer, preferably the compound (Ia),is isolated in a stereochemical purity of from 60 to 100%, preferablyfrom 70 to 100%, more preferably from 80 to 100%, in particular from 90to 100%, based on the mixture of the erythro and threo enantiomerspresent.

As an alternative to the optical resolution methods mentioned,enantioselective processes starting with stereochemically pure startingmaterials are in principle also suitable for preparing the opticallyactive enantiomers, preferably the threo-2 enantiomers (Ia).

The following acids are generally suitable for preparing the acidaddition salts of the compounds of the formula (I): hydrohalic acids,such as hydrochloric acid or hydrobromic acid, furthermore phosphoricacid, nitric acid, sulphuric acid, mono- or bifunctional carboxylicacids and hydroxycarboxylic acids, such as acetic acid, maleic acid,succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid,sorbic acid, or lactic acid, and also sulphonic acids, such asp-toluenesulphonic acid and 1,5-naphthalenedisulphonic acid. The acidaddition compounds of the formula (I) can be obtained in a simple mannerby the customary methods for forming salts, for example by dissolving acompound of the formula (I) in a suitable organic solvent, such as, forexample, methanol, acetone, methylene chloride or benzene, and addingthe acid at temperatures of from 0 to 100° C., and they can be isolatedin a known manner, for example by filtration, and, if appropriate,purified by washing with an inert organic solvent.

The base addition salts of the compounds of the formula (I) arepreferably prepared in inert polar solvents, such as, for example,water, methanol or acetone, at temperatures of from 0 to 100° C.Examples of bases which are suitable for the preparation of the saltsaccording to the invention are alkali metal carbonates, such aspotassium carbonate, alkali metal hydroxides and alkaline earth metalhydroxides, for example NaOH or KOH, alkali metal hydrides and alkalineearth metal hydrides, for example NaH, alkali metal alkoxides andalkaline earth metal alkoxides, for example sodium methoxide orpotassium tert-butoxide, or ammonia, ethanolamine or quaternary ammoniumhydroxide of the formula [NRR′R″R′″]⁺OH⁻.

Collections of compounds of the formula (I) which can be synthesized bythe aforementioned process can also be prepared in a parallel manner, itbeing possible for this to take place in a manual, partly automated orcompletely automated manner. In this connection, it is possible toautomate the reaction procedure, the work-up or the purification of theproducts and/or intermediates. Overall, this is understood as meaning aprocedure as described, for example, by S. H. DeWitt in “Annual Reportsin Combinatorial Chemistry and Molecular Diversity: AutomatedSynthesis”, Volume 1, Verlag Escom, 1997, pages 69 to 77.

For the parallelized reaction procedure and workup it is possible to usea range of commercially available instruments, of the kind offered by,for example, the companies Stem Corporation, Woodrolfe Road, Tollesbury,Essex, CM9 8SE, England, or H+P Labortechnik GmbH, Bruckmannring 28,85764 Oberschleiβheim, Germany. For the parallel purification ofcompounds (I) or of intermediates produced during the preparation, thereare available, inter alia, chromatography apparatuses, for example fromISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA. Theapparatuses listed allow a modular procedure in which the individualprocess steps are automated, but between the process steps manualoperations have to be carried out. This can be circumvented by usingpartly or completely integrated automation systems in which therespective automation modules are operated, for example, by robots.Automation systems of this type can be acquired, for example, fromZymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

Besides the methods described here, the preparation of compounds of theformula (I) can take place completely or partially by solid-phasesupported methods. For this purpose, individual intermediates or allintermediates in the synthesis or a synthesis adapted for thecorresponding procedure are bound to a synthesis resin.Solid-phase-supported synthesis methods are described extensively in thespecialist literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998.

The use of solid-phase-supported synthesis methods permits a number ofprotocols, which are known from the literature and which for their partmay be performed manually or in an automated manner, to be carried out.For example, the “teabag method” (Houghten, U.S. Pat. No. 4,631,211;Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135) in whichproducts from IRORI, 11149 North Torrey Pines Road, La Jolla, Calif.92037, USA, are employed, may be semiautomated. The automation ofsolid-phase-supported parallel syntheses is performed successfully, forexample, by apparatuses from Argonaut Technologies, Inc., 887 IndustrialRoad, San Carlos, Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld4, 58454 Witten, Germany.

The preparation according to the processes described herein producescompounds of the formula (I) in the form of substance collections orlibraries. Accordingly, the present invention also provides libraries ofcompounds of the formula (I) which comprise at least two compounds ofthe formula (I), and precursors thereof.

The compounds of the formula (I) according to the invention (and/ortheir salts), above and hereinbelow also referred to together as“compounds according to the invention”, “compounds (I) according to theinvention” or in short as “compounds (I)”, have excellent herbicidalefficacy against a broad spectrum of economically importantmonocotyledonous and dicotyledonous annual harmful plants. The activecompounds also have good control over perennial harmful plants which aredifficult to control and produce shoots from rhizomes, root stocks orother perennial organs.

The present invention therefore also relates to a method for controllingunwanted plants or for regulating the growth of plants, preferably incrops of plants, where one or more compound(s) according to theinvention is/are applied to the plants (for example harmful plants suchas monocotyledonous or dicotyledonous weeds or undesired crop plants),to the seed (for example grains, seeds or vegetative propagules such astubers or shoot parts with buds), to the soil in or on which the plantsgrow (for example the soil of cropland or non-cropland) or to the areaon which the plants grow (for example the area under cultivation). Inthis context, the compounds according to the invention can be appliedfor example in pre-sowing (if appropriate also by incorporation into thesoil), pre-emergence or post-emergence. Specific examples may bementioned of some representatives of the monocotyledonous anddicotyledonous weed flora which can be controlled by the compoundsaccording to the invention, without the enumeration being restricted tocertain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

When the compounds according to the invention are applied to the soilsurface before germination, either the weed seedlings are preventedcompletely from emerging or the weeds grow until they have reached thecotyledon stage, but then stop growing and eventually, after three tofour weeks have elapsed, die completely.

If the active ingredients are applied post-emergence to the green partsof the plants, growth stops after the treatment, and the harmful plantsremain at the growth stage of the time of application, or die completelyafter a certain time, such that competition by the weeds, which isharmful to the crop plants, is thus eliminated very early and in alasting manner.

Although the compounds according to the invention display an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example dicotyledonouscrops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita,Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia,or monocotyledonous crops of the genera Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea, in particular Zea and Triticum, are damaged only to aninsignificant extent, or not at all, depending on the structure of therespective compound according to the invention and its application rate.For these reasons, the present compounds are very suitable for selectivecontrol of unwanted plant growth in plant crops such as agriculturallyuseful plants or ornamentals.

In addition, the compounds according to the invention (depending ontheir particular structure and the application rate deployed) haveoutstanding growth-regulating properties in crop plants. They interveneto regulate the plant's metabolism and can thus be used for controlledinfluence on plant constituents and to facilitate harvesting, forexample by triggering desiccation and stunted growth. In addition, theyare also suitable for general control and inhibition of unwantedvegetative growth without killing the plants. Inhibiting the vegetativegrowth plays an important role in many monocotyledonous anddicotyledonous crops since for example lodging can be reduced, orprevented completely, hereby.

By virtue of their herbicidal and plant growth-regulating properties,the active compounds can also be used for control of harmful plants incrops of genetically modified plants or plants modified by conventionalmutagenesis. In general, the transgenic plants are distinguished byespecially advantageous properties, for example by resistances tocertain pesticides, mainly certain herbicides, resistances to plantdiseases or causative organisms of plant diseases, such as certaininsects or microorganisms such as fungi, bacteria or viruses. Otherspecific characteristics relate, for example, to the harvested materialwith regard to quantity, quality, storability, composition and specificconstituents. Thus, transgenic plants are known whose starch content isincreased, or whose starch quality is altered, or those where theharvested material has a different fatty acid composition.

It is preferred with a view to trangenic crops to use the compoundsaccording to the invention and/or their salts in economically importanttransgenic crops of useful plants and ornamentals, for example ofcereals such as wheat, barley, rye, oats, millet, rice and corn or elsecrops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peasand other vegetables.

It is preferred to employ the compounds according to the invention asherbicides in crops of useful plants which are resistant, or have beenmade resistant by recombinant means, to the phytotoxic effects of theherbicides.

By virtue of their herbicidal and plant-growth-regulatory properties,the active compounds can also be employed for controlling harmful plantsin crops of known genetically modified plants or genetically modifiedplants still to be developed. In general, the transgenic plants aredistinguished by especially advantageous properties, for example byresistances to certain pesticides, mainly certain herbicides,resistances to plant diseases or causative organisms of plant diseases,such as certain insects or microorganisms such as fungi, bacteria orviruses. Other specific characteristics relate, for example, to theharvested material with regard to quantity, quality, storability,composition and specific constituents. Thus, transgenic plants are knownwhose starch content is increased, or whose starch quality is altered,or those where the harvested material has a different fatty acidcomposition. Other particular properties may be tolerance or resistanceto abiotic stressors, for example heat, low temperatures, drought,salinity and ultraviolet radication.

It is preferred to use the compounds of the formula (I) according to theinvention or salts thereof in economically important transgenic crops ofuseful plants and ornamental plants, for example of cereals such aswheat, barley, rye, oats, millet, rice, cassava and corn or else cropsof sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas andother vegetables.

It is preferred to employ the compounds of the formula (I) according tothe invention as herbicides in crops of useful plants which areresistant, or have been made resistant by recombinant means, to thephytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to plants which have occurred to date consist,for example, in traditional breeding methods and the generation ofmutants. Alternatively, novel plants with altered properties can begenerated with the aid of recombinant methods (see, for example,EP-A-0221044, EP-A-0131624). For example, the following have beendescribed in several cases:

-   -   recombinant modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (for example WO        92/11376, WO 92/14827, WO 91/19806).    -   transgenic crop plants which are resistant to particular        herbicides of the glufosinate type (cf., for example,        EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or        the sulphonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, which is capable of        producing Bacillus thuringiensis toxins (Bt toxins), which make        the plants resistant to certain pests (EP-A-0142924,        EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 309862,        EPA0464461),    -   genetically modified plants with reduced photorespiration which        feature higher yields and higher stress tolerance (EPA 0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which are distinguished by higher yields        or better quality,    -   transgenic crop plants which are distinguished by a combination,        for example of the abovementioned novel properties (“gene        stacking”).

A large number of molecular-biological techniques by means of whichnovel transgenic plants with modified properties can be generated areknown in principle; see, for example, I. Potrykus and G. Spangenberg(eds.) Gene Transfer to Plants, Springer Lab Manual (1995), SpringerVerlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1(1996) 423-431.

For such recombinant manipulations, nucleic acid molecules which allowmutagenesis or a sequence change by recombination of DNA sequences canbe introduced into plasmids. For example, base substitutions can becarried out, part-sequences can be removed, or natural or syntheticsequences may be added with the aid of standard methods. For the joiningof the DNA fragments to one another, adaptors or linkers can be attachedto the fragments; see, for example, Sambrook et al., 1989, MolecularCloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor LaboratoryPress, Cold Spring Harbor, N.Y.; or Winnacker “Gene and Klone” [Genesand Clones], VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product. For thispurpose, it is firstly possible to use DNA molecules which comprise theentire coding sequence of a gene product including any flankingsequences present, or else DNA molecules which comprise only parts ofthe coding sequence, in which case these parts must be long enough tobring about an antisense effect in the cells. It is also possible to useDNA sequences which have a high degree of homology to the codingsequences of a gene product, but are not completely identical.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to link the coding region with DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Thenucleic acid molecules can also be expressed in the organelles of theplant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants may beplants of any desired plant species, i.e. both monocotyledonous anddicotyledonous plants.

Thus, it is possible to obtain transgenic plants whose properties arealtered by overexpression, suppression or inhibition of homologous(=natural) genes or gene sequences, or expression of heterologous(=foreign) genes or gene sequences.

It is preferred to employ the compounds (I) according to the inventionin transgenic crops which are resistant to growth regulators such as,for example, dicamba, or against herbicides which inhibit essentialplant enzymes, for example acetolactate synthases (ALS), EPSP synthases,glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD),or against herbicides from the group consisting of the sulphonylureas,glyphosate, glufosinate or benzoylisoxazoles and analogous activecompounds.

On employment of the inventive active ingredients in transgenic crops,not only do the effects toward harmful plants observed in other cropsoccur, but often also effects which are specific to application in theparticular transgenic crop, for example an altered or specificallywidened spectrum of weeds which can be controlled, altered applicationrates which can be used for the application, preferably goodcombinability with the herbicides to which the transgenic crop isresistant, and influencing of growth and yield of the transgenic cropplants.

The invention therefore also relates to the use of the compounds of theformula (I) according to the invention and/or their salts as herbicidesfor controlling harmful plants in crops of useful plants or ornamentals,optionally in transgenic crop plants. Preference is given to the use bythe pre- or post-emergence method in cereals such as wheat, barley, rye,oats, millet and rice, in particular in wheat by the post-emergencemethod.

Preference is also given to the use by the pre- or post-emergence methodin corn, in particular by the pre-emergence method in corn.

Preference is also given to the use by the pre- or post-emergence methodin soybeans, in particular by the post-emergence method in soybeans.

The use according to the invention for the control of harmful plants orfor growth regulation of plants also includes the case in which theactive compound of the formula (I) or its salt is not formed from aprecursor substance (“prodrug”) until after application on the plant, inthe plant or in the soil.

The invention also provides the method (application method) forcontrolling harmful plants or for regulating the growth of plants whichcomprises applying an effective amount of one or more compounds of theformula (I) or salts thereof onto the plants (harmful plants, ifappropriate together with the useful plants), plant seeds, the soil inwhich or on which the plants grow or the area under cultivation.

The compounds (I) according to the invention can be used in the form ofwettable powders, emulsifiable concentrates, sprayable solutions,dusting products or granules in the customary formulations. Theinvention therefore also provides herbicidal and plant growth-regulatingcompositions which comprise compounds of the formula (I) and/or saltsthereof.

The compounds of the formula (I) and/or salts thereof can be formulatedin various ways according to which biological and/or physicochemicalparameters are required. Possible formulations include, for example:wettable powders (WP), water-soluble powders (SP), water-solubleconcentrates, emulsifiable concentrates (EC), emulsions (EW), such asoil-in-water and water-in-oil emulsions, sprayable solutions, suspensionconcentrates (SC), oil- or water-based dispersions, oil-misciblesolutions, capsule suspensions (CS), dusting products (DP),seed-dressing products, granules for broadcasting and soil application,granules (GR) in the form of microgranules, sprayable granules, coatedgranules and adsorption granules, water-dispersible granules (WG),water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical technology], volume 7, C. Hanser Verlag Munich, 4th ed. 1986;Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd.London.

The necessary formulation aids, such as inert materials, surfactants,solvents and further additives are likewise known and are described, forexample, in: Watkins, “Handbook of Insecticide Dust Diluents andCarriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen,“Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons,N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963;McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene OxideAdducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie”, volume 7, C. Hanser Verlag Munich, 4th ed.1986.

Wettable powders are preparations which can be dispersed uniformly inwater and, as well as the active compound, apart from a diluent or inertsubstance, also comprise surfactants of the ionic and/or nonionic type(wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulphates, alkanesulphonates,alkylbenzenesulphonates, sodium lignosulphonate, sodium2,2′-dinaphthylmethane-6,6′-disulphonate, sodiumdibutylnaphthalenesulphonate or else sodium oleoylmethyltaurinate. Toprepare the wettable powders, the herbicidally active compounds areground finely, for example in customary apparatus such as hammer mills,blower mills and air-jet mills, and simultaneously or subsequently mixedwith the formulation assistants.

Emulsifiable concentrates are produced by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more surfactants of the ionic and/or nonionic type (emulsifiers). Theemulsifiers used may, for example, be: alkylarylsulphonic calcium salts,such as calcium dodecylbenzenesulphonate, or nonionic emulsifiers suchas fatty acid polyglycol esters, alkylaryl polyglycol ethers, fattyalcohol polyglycol ethers, propylene oxide-ethylene oxide condensationproducts, alkyl polyethers, sorbitan esters, such as, for example,sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as,for example, polyoxyethylene sorbitan fatty acid esters.

Dusting products are obtained by grinding the active compound withfinely distributed solid substances, for example talc, natural clays,such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They can beproduced, for example, by wet grinding by means of commercial bead millswith optional addition of surfactants as already listed above, forexample, for the other formulation types.

Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and if appropriate surfactants, as have forexample already been listed above in connection with the other types offormulation.

Granules can be produced either by spraying the active compound ontoadsorptive granulated inert material or by applying active compoundconcentrates by means of adhesives, for example polyvinyl alcohol,sodium polyacrylate or mineral oils, to the surface of carriersubstances, such as sand, kaolinites or of granulated inert material.Suitable active compounds can also be granulated in the manner customaryfor the production of fertilizer granules—if desired as a mixture withfertilizers.

Water-dispersible granules are produced generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan granules, fluidized bed granules, extrudergranules and spray granules, see, for example, processes in“Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E.Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.;“Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York1973, pp. 8-57.

For further details regarding the formulation of crop protection agents,see, for example, G. C. Klingman, “Weed Control as a Science”, JohnWiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S.A. Evans, “Weed Control Handbook”, 5th ed., Blackwell ScientificPublications, Oxford, 1968, pages 101-103.

The agrochemical formulations comprise generally from 0.1 to 99% byweight, in particular from 0.1 to 95% by weight, of active compound ofthe formula (I) and/or salts thereof.

In wettable powders, the active compound concentration is, for example,about 10 to 90% by weight; the remainder to 100% by weight consists ofthe customary formulation constituents. In emulsifiable concentrates,the active ingredient concentration may be about 1 to 90% and preferably5 to 80% by weight. Dust-type formulations contain from 1 to 30% byweight of active compound, preferably usually from 5 to 20% by weight ofactive compound; sprayable solutions contain from about 0.05 to 80% byweight, preferably from 2 to 50% by weight of active compound. In thecase of water-dispersible granules, the active compound content dependspartly on whether the active compound is present in liquid or solid formand on which granulation assistants, fillers, etc., are used. In thewater-dispersible granules, the content of active compound is, forexample, between 1 and 95% by weight, preferably between 10 and 80% byweight.

In addition, the active ingredient formulations mentioned optionallycomprise the respective customary tackifiers, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agentsand solvents, fillers, carriers and dyes, defoamers, evaporationinhibitors and agents which influence the pH and the viscosity. Examplesof formulation auxiliaries are described, inter alia, in “Chemistry andTechnology of Agrochemical Formulations”, ed. D. A. Knowles, KluwerAcademic Publishers (1998).

The compounds of the formula (I) or salts thereof can be employed assuch or in the form of their preparations (formulations) combined withother pesticidally active compounds, such as, for example, insecticides,acaricides, nematicides, herbicides, fungicides, safeners, fertilizersand/or growth regulators, for example as finished formulation or as tankmixes. The combination formulations can be prepared on the basis of theabovementioned formulations, while taking account of the physicalproperties and stabilities of the active compounds to be combined.

Combination partners for the compounds according to the invention inmixed formulations or in the tank mix are, for example, known activecompounds which are based on the inhibition of, for example,acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase,enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase,p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase, photosystem I,photosystem II, protoporphyrinogen oxidase, as are described in, forexample, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 15thedition, The British Crop Protection Council and the Royal Soc. ofChemistry, 2006 and the literature cited therein. Known herbicides orplant growth regulators which can be combined with the compoundsaccording to the invention are, for example, the following activecompounds (the compounds are either designated by the common nameaccording to the International Organization for Standardization (ISO) orby the chemical name, or by the code number) and always comprise all useforms such as acids, salts, esters and isomers such as stereoisomers andoptical isomers. In this case, one or else, in some cases, more than oneuse form is mentioned by way of example: acetochlor, acibenzolar,acibenzolar-5-methyl, acifluorfen, acifluorfen-sodium, aclonifen,alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryne,amicarbazone, amidochlor, amidosulphuron, aminocyclopyrachlor,aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid,amitrole, ammonium sulphamate, ancymidol, anilofos, asulam, atrazine,azafenidin, azimsulphuron, aziprotryne, beflubutamid, benazolin,benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide,bensulphuron, bensulphuron-methyl, bentazone, benzfendizone,benzobicyclon, benzofenap, benzofluor, benzoylprop, bicyclopyrone,bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium,bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos,busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin,butroxydim, butylate, cafenstrole, carbetamide, carfentrazone,carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop,chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac,chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl,chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride,chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlortoluron,chlorsulphuron, cinidon, cinidon-ethyl, cinmethylin, cinosulphuron,clethodim, clodinafop, clodinafop-propargyl, clofencet,clofencet-potassium, clomazone, clomeprop, cloprop, clopyralid,cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine,cyclanilide, cycloate, cyclosulphamuron, cycloxydim, cycluron,cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D,2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol,desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba,dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl,diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron,difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium,dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimethenamid-P, dimethipin, dimetrasulphuron, dinitramine,dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide,dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb,ethalfluralin, ethametsulphuron, ethametsulphuron-methyl, ethephon,ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl,ethoxysulphuron, etobenzanid, F-5331, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulphonamide,F-7967, i.e.3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione,fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl,fenoxaprop-P-ethyl, fenoxasulphone, fentrazamide, fenuron, flamprop,flamprop-M-isopropyl, flamprop-M-methyl, flazasulphuron, florasulam,fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate,flucarbazone, flucarbazone-sodium, flucetosulphuron, fluchloralin,flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin,flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn,fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl,flupoxam, flupropacil, flupropanate, flupyrsulphuron,flupyrsulphuron-methyl-sodium, flurenol, flurenol-butyl, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol,flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen,foramsulphuron, forchlorfenuron, fosamine, furyloxyfen, gibberellicacid, glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate,glyphosate-isopropylammonium, H-9201, i.e.O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate,halosafen, halosulphuron, halosulphuron-methyl, haloxyfop, haloxyfop-P,haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl,haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl(2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl,imazamox, imazamox-ammonium, imazapic, imazapyr,imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr,imazethapyr-ammonium, imazosulphuron, inabenfide, indanofan, indaziflam,indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulphuron,iodosulphuron-methyl-sodium, iofensulphuron, iofensulphuron-sodium,ioxynil, ipfencarbazone, isocarbamid, isopropalin, isoproturon, isouron,isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, i.e.3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulphonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole,karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide,MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium,mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium,mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide,mepiquat-chloride, mesosulphuron, mesosulphuron-methyl, mesotrione,methabenzthiazuron, metam, metamifop, metamitron, metazachlor,metazasulphuron, methazole, methiopyrsulphuron, methiozolin,methoxyphenone, methyldymron, 1-methylcyclopropene, methylisothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor,metosulam, metoxuron, metribuzin, metsulphuron, metsulphuron-methyl,molinate, monalide, monocarbamide, monocarbamide dihydrogensulphate,monolinuron, monosulphuron, monosulphuron ester, monuron, MT-128, i.e.6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazine-3-amine,MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide,NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon,nicosulphuron, nipyraclofen, nitralin, nitrofen, nitrophenolate-sodium(isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb,orthosulphamuron, oryzalin, oxadiargyl, oxadiazon, oxasulphuron,oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquatdichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin,penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid,phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen,pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor,primisulphuron, primisulphuron-methyl, probenazole, profluazole,procyazine, prodiamine, prifluraline, profoxydim, prohexadione,prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor,propanil, propaquizafop, propazine, propham, propisochlor,propoxycarbazone, propoxycarbazone-sodium, propyrisulphuron,propyzamide, prosulphalin, prosulphocarb, prosulphuron, prynachlor,pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulphotole, pyrazolynate(pyrazolate), pyrazosulphuron, pyrazosulphuron-ethyl, pyrazoxyfen,pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim,pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac,pyriminobac-methyl, pyrimisulphan, pyrithiobac, pyrithiobac-sodium,pyroxasulphone, pyroxsulam, quinclorac, quinmerac, quinoclamine,quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, rimsulphuron, saflufenacil, secbumeton,sethoxydim, siduron, simazine, simetryn, SN-106279, i.e. methyl(2R)-2-({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propanoate,sulcotrione, sulphallate (CDEC), sulphentrazone, sulphometuron,sulphometuron-methyl, sulphosate (glyphosate-trimesium),sulphosulphuron, SW-065, SYN-523, SYP-249, i.e.1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e.1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione,tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,terbuthylazine, terbutryne, thenylchlor, thiafluamide, thiazafluoron,thiazopyr, thidiazimin, thidiazuron, thiencarbazone,thiencarbazone-methyl, thifensulphuron, thifensulphuron-methyl,thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone,triallate, triasulphuron, triaziflam, triazofenamide, tribenuron,tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane,trietazine, trifloxysulphuron, trifloxysulphuron-sodium, trifluralin,triflusulphuron, triflusulphuron-methyl, trimeturon, trinexapac,trinexapac-ethyl, tritosulphuron, tsitodef, uniconazole, uniconazole-P,vernolate, ZJ-0862, i.e.3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, andthe following compounds:

Of particular interest is the selective control of harmful plants incrops of useful plants and ornamentals. Although the compounds (I)according to the invention have already demonstrated very good toadequate selectivity in a large number of crops, in principle, in somecrops and in particular also in the case of mixtures with other, lessselective herbicides, phytotoxicities on the crop plants may occur. Inthis connection, combinations of compounds (I) according to theinvention are of particular interest which comprise the compounds (I) ortheir combinations with other herbicides or pesticides and safeners. Thesafeners, which are used in an antidotically effective amount, reducethe phytotoxic side effects of the herbicides/pesticides employed, forexample in economically important crops, such as cereals (wheat, barley,rye, corn, rice, millet), sugar beet, sugar cane, oilseed rape, cottonand soybeans, preferably cereals. The following groups of compounds aresuitable, for example, as safeners for the compounds (I) and theircombinations with further pesticides:

A) compounds of the formula (S-I)

where the symbols and indices have the following meanings:

-   n_(A) is a natural number from 0 to 5, preferably from 0 to 3;-   R_(A) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or    (C₁-C₄)-haloalkyl;-   W_(A) is an unsubstituted or substituted divalent heterocyclic    radical from the group consisting of the partially unsaturated or    aromatic five-membered heterocycles having 1 to 3 ring heteroatoms    of the N or O type, where at least one nitrogen atom and at most one    oxygen atom is present in the ring, preferably a radical from the    group consisting of (W_(A) ¹) to (W_(A) ⁴),

-   m_(A) is 0 or 1;-   R_(A) ² is OR_(A) ³, SR_(A) ³ or NR_(A) ³R_(A) ⁴ or a saturated    -   or unsaturated 3- to 7-membered heterocycle having at least one        nitrogen atom and up to 3 heteroatoms, preferably from the group        consisting of O and S, which is joined to the carbonyl group in        (S-1) via the nitrogen atom and is unsubstituted or substituted        by radicals from the group consisting of (C₁-C₄)-alkyl,        (C₁-C₄)-alkoxy or optionally substituted phenyl, preferably a        radical of the formula OR_(A) ³, NH R_(A) ⁴ or N(CH₃)₂,        especially of the formula OR_(A) ³;-   R_(A) ³ is hydrogen or an unsubstituted or substituted aliphatic    hydrocarbyl radical preferably having a total of 1 to 18 carbon    atoms;-   R_(A) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or    unsubstituted phenyl;-   R_(A) ⁵ is H, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,    (C₁-C₄)-alkoxy(C₁-C₈)-alkyl, cyano or COOR_(A) ⁹ in which R_(A) ⁹ is    hydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-hydroxyalkyl,    (C₃-C₁₂)-cycloalkyl or tri-(C₁-C₄)-alkylsilyl;-   R_(A) ⁶, R_(A) ⁷, R_(A) ⁸ are identical or different and are    hydrogen, (C₁-C₈)-alkyl,    -   (C₁-C₈)-haloalkyl, (C₃-C₁₂)-cycloalkyl or substituted or        unsubstituted phenyl;        preferably:-   a) compounds of the type of the    dichlorophenylpyrazoline-3-carboxylic acid, preferably compounds    such as ethyl    1-2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate    (S1-1) (“mefenpyr-diethyl”, see Pestic. Man.), and related compounds    as described in WO 91/07874;-   b) derivatives of dichlorophenylpyrazolecarboxylic acid, preferably    compounds such as ethyl    1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl    1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3),    ethyl    1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate    (S1-4), ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate    (S1-5) and related compounds as described in EP-A-333 131 and    EP-A-269 806;-   c) compounds of the triazolecarboxylic acid type, preferably    compounds such as fenchlorazole(-ethyl), i.e. ethyl    1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate    (S1-6), and related compounds as described in EP-A-174 562 and    EP-A-346 620;-   d) compounds of the type of the 5-benzyl- or    5-phenyl-2-isoxazoline-3-carboxylic acid or the    5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds    such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate    (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and    related compounds, as described in WO 91/08202, or ethyl    5,5-diphenyl-2-isoxazolinecarboxylate (S1-9) (“isoxadifen-ethyl”) or    n-propyl 5,5-diphenyl-2-isoxazolinecarboxylate (S1-10) or ethyl    5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-11), as    described in the patent application WO-A-95/07897.    B) Quinoline derivatives of the formula (S-II)

where the symbols and indices have the following meanings:

-   R_(B) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or    (C₁-C₄)-haloalkyl;-   n_(B) is a natural number from 0 to 5, preferably from 0 to 3;-   R_(B) ² is OR_(B) ^(S), SR_(B) ³ or NR_(B) ³R_(B) ⁴ or a saturated    or unsaturated 3- to 7-membered heterocycle having at least one    nitrogen atom and up to 3 heteroatoms, preferably from the group    consisting of O and S, which is joined to the carbonyl group in    (S-II) via the nitrogen atom and is unsubstituted or substituted by    radicals from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy    or optionally substituted phenyl, preferably a radical of the    formula OR_(B) ³, NH R^(e) or N(CH₃)₂, especially of the formula    OR_(B) ³;-   R_(B) ³ is hydrogen or an unsubstituted or substituted aliphatic    hydrocarbyl radical preferably having a total of 1 to 18 carbon    atoms;-   R_(B) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or    unsubstituted phenyl;-   T_(B) is a (C₁ or C₂)-alkanediyl chain which is unsubstituted or    substituted by one or two (C₁-C₄)-alkyl radicals or by    [(C₁-C₃)-alkoxy]carbonyl;    preferably:-   a) compounds of the 8-quinolinoxyacetic acid type (S2), preferably    -   1-methylhexyl 5-chloro-8-quinolinoxyacetate (common name        “cloquintocet-mexyl” (S2-1) (see Pestic. Man.),    -   1,3-dimethylbut-1-yl 5-chloro-8-quinolinoxyacetate (S2-2),    -   4-allyloxybutyl 5-chloro-8-quinolinoxyacetate (S2-3),    -   1-allyloxyprop-2-yl 5-chloro-8-quinolinoxyacetate (S2-4),    -   ethyl 5-chloro-8-quinolinoxyacetate (S2-5),    -   methyl 5-chloro-8-quinolinoxyacetate (S2-6),    -   allyl 5-chloro-8-quinolinoxyacetate (S2-7),    -   2-(2-propylideneiminoxy)-1-ethyl 5-chloro-8-quinolinoxyacetate        (S2-8), 2-oxoprop-1-yl 5-chloro-8-quinolinoxyacetate (S2-9) and        related compounds as described in EP-A-86 750, EP-A-94 349 and        EP-A-191 736 or EP-A-0 492 366, and also their hydrates and        salts as described in WO-A-2002/034048.-   b) compounds of the (5-chloro-8-quinolinoxy)malonic acid type,    preferably compounds such as diethyl    (5-chloro-8-quinolinoxy)malonate, diallyl    (5-chloro-8-quinolinoxy)malonate, methyl ethyl    (5-chloro-8-quinolinoxy)malonate and related compounds, as described    in EP-A-0 582 198.-   C) Compounds of the formula (S-III)

where the symbols and indices have the following meanings:

-   R_(C) ¹ is (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₃-C₇)-cycloalkyl, preferably dichloromethyl;-   R_(C) ², R_(C) ³ are identical or different and are hydrogen,    (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-haloalkyl,    (C₂-C₄)-haloalkenyl, (C₁-C₄)-alkylcarbamoyl-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenylcarbamoyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, dioxolanyl-(C₁-C₄)-alkyl, thiazolyl,    furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted    phenyl, or R_(C) ² and R_(C) ³ together form a substituted or    unsubstituted heterocyclic ring,    -   preferably an oxazolidine, thiazolidine, piperidine, morpholine,    -   hexahydropyrimidine or benzoxazine ring;        preferably:    -   active compounds of the dichloroacetamide type which are        frequently used as pre-emergence safeners (soil-active        safeners), such as, for example, “dichlormid” (see Pestic. Man.)        (=N,N-diallyl-2,2-dichloroacetamide),    -   “R-29148” (=3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine        from Stauffer),    -   “R-28725” (=3-dichloroacetyl-2,2,-dimethyl-1,3-oxazolidine from        Stauffer), “benoxacor” (see Pestic. Man.)        (=4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine),    -   “PPG-1292”        (=N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide from        PPG Industries),    -   “DKA-24”        (=N-allyl-N—[(allylaminocarbonyl)methyl]dichloroacetamide from        Sagro-Chem),    -   “AD-67” or “MON 4660”        (=3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane from Nitrokemia        or Monsanto),    -   “TI-35” (=1-dichloroacetylazepane from TRI-Chemical RT)    -   “diclonon” (dicyclonon) or “BAS145138” or “LAB145138”        (=3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane        from BASF) and    -   “furilazole” or “MON 13900” (see Pestic. Man.)        (=(RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine)        D) N-Acylsulphonamides of the formula (S-IV) and their salts

in which

-   R_(D) ¹ is hydrogen, a hydrocarbon radical, a hydrocarbonoxy    radical, a hydrocarbonthio radical or a heterocyclyl radical which    is preferably attached via a carbon atom, where each of the 4    last-mentioned radicals is unsubstituted or substituted by one or    more identical or different radicals from the group consisting of    halogen, cyano, nitro, amino, hydroxy, carboxy, formyl, carboxamide,    sulphonamide and radicals of the formula —Z^(a)—R^(a),    -   where each hydrocarbon moiety has preferaby 1 to 20 carbon atoms        and a carbon-containing radical R_(D) ¹ including substituents        has preferably 1 to 30 carbon atoms;-   R_(D) ² is hydrogen or (C₁-C₄)-alkyl, preferably hydrogen, or-   R_(D) ¹ and R_(D) ² together with the group of the formula —CO—N—    are the radical of a 3- to 8-membered saturated or unsaturated ring;-   R_(D) ³ are identical or different and are halogen, cyano, nitro,    amino, hydroxy, carboxy, formyl, CON H₂, SO₂NH₂ or a radical of the    formula —Z^(b)—R^(b);-   R_(D) ⁴ is hydrogen or (C₁-C₄)-alkyl, preferably H;-   R_(D) ⁵ are identical or different and are halogen, cyano, nitro,    amino, hydroxy, carboxy, CHO, CON H₂, SO₂NH₂ or a radical of the    formula —Z^(c)—R^(c);-   R^(a) is a hydrocarbon radical or a heterocyclyl radical, where each    of the two last-mentioned radicals is unsubstituted or substituted    by one or more identical or different radicals from the group    consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and    di-[(C₁-C₄)-alkyl]amino, or an alkyl radical in which a plurality,    preferably 2 or 3, non-adjacent CH₂ groups are in each case replaced    by an oxygen atom;-   R^(b), R^(c) are identical or different and are a hydrocarbon    radical or a heterocyclyl radical, where each of the two    last-mentioned radicals is unsubstituted or substituted by one or    more identical or different radicals from the group consisting of    halogen, cyano, nitro, amino, hydroxy, phosphoryl,    halo-(C₁-C₄)-alkoxy, mono- and di-[(C₁-C₄)-alkyl]amino, or an alkyl    radical in which a plurality, preferably 2 or 3, non-adjacent CH₂    groups are in each case replaced by an oxygen atom;-   Z^(a) is a divalent group of the formula —O—, —S—, —CO—, —CS—,    —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO₂—, —NR*—, —CO—NR*—,    —NR*—CO—, —SO₂—NR*— or —NR*—SO₂—, where the bond indicated on the    right-hand side of the divalent group in question is the bond to the    radical R^(a) and where the R* in the 5 last-mentioned radicals    independently of one another are each H, (C₁-C₄)-alkyl or    halo-(C₁-C₄)-alkyl;-   Z^(b), Z^(c) are independently of one another a direct bond or a    divalent group of the formula —O—, -5-, —CO—, —CS—, —CO—O—, —CO—S—,    —O—CO—,    -   —S—CO—, —SO—, —SO₂—, —NR*—, —SO₂—NR*—, —NR*—SO₂—, —CO—NR*—    -   or —NR*—CO—, where the bond indicated at the right-hand side of        the divalent group in question is the bond to the radical R^(b)        or R^(c) and where the R* in the 5 last-mentioned radicals        independently of one another are each H, (C₁-C₄)-alkyl or        halo-(C₁-C₄)-alkyl;-   n_(D) is an integer from 0 to 4, preferably 0, 1 or 2, particularly    preferably 0 or 1, and-   m_(D) is an integer from 0 to 5, preferably 0, 1, 2 or 3, in    particular 0, 1 or 2;    E) acylsulphamoylbenzamides of the formula (S-V), if appropriate    also in salt form,

in which

-   X_(E) is CH or N,-   R_(E) ¹ is hydrogen, heterocyclyl or a hydrocarbon radical, where    the two last-mentioned radicals are optionally substituted by one or    more identical or different radicals from the group consisting of    halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH₂, SO₂NH₂    and Z^(a)—R^(a);-   R_(E) ² is hydrogen, hydroxy, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkynyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, where the five    last-mentioned radicals are optionally substituted by one or more    identical or different radicals from the group consisting of    halogen, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and    (C₁-C₄)-alkylthio, or-   R_(E) ¹ and R_(E) ² together with the nitrogen atom that carries    them are a 3- to 8-membered saturated or unsaturated ring;-   R_(E) ³ is halogen, cyano, nitro, amino, hydroxy, carboxy, CHO,    CONH₂, SO₂NH₂ or Z^(b)—R¹³,-   R_(E) ⁴ is hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or    (C₂-C₄)-alkynyl;-   R_(E) ⁵ is halogen, cyano, nitro, amino, hydroxy, carboxy,    phosphoryl, CHO, CONH₂, SO₂NH₂ or Z^(c)—R^(c);-   R^(a) is a (C₂-C₂₀)-alkyl radical whose carbon chain is interrupted    once or more than once by    -   oxygen atoms, is heterocyclyl or a hydrocarbon radical, where        the two last-mentioned radicals are optionally substituted by        one or more identical or different radicals from the group        consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and        di-[(C₁-C₄)-alkyl]-amino;-   R^(b), R^(c) are identical or different and are a (C₂-C₂₀)-alkyl    radical whose carbon chain is interrupted once or more than once by    oxygen atoms, are heterocyclyl or a hydrocarbon radical, where the    two last-mentioned radicals are optionally substituted by one or    more identical or different radicals from the group consisting of    halogen, cyano, nitro, amino, hydroxyl, phosphoryl,    (C₁-C₄)-haloalkoxy, mono- and di-[(C₁-C₄)-alkyl]amino;-   Z^(a) is a divalent unit from the group consisting of O, S, CO, CS,    C(O)O, C(O)S, SO, SO₂, NR^(d), C(O)NR^(d) and SO₂NR^(d);-   Z^(b), Z^(c) are identical or different and are a direct bond or    divalent unit from the group consisting of    -   O, S, CO, CS, C(O)O, C(O)S, SO, SO₂, NR^(d), SO₂NR^(d) and        C(O)NR^(d);-   R^(d) is hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-haloalkyl;-   n_(E) is an integer from 0 to 4, and-   m_(E) if X is CH, is an integer from 0 to 5, and, if X is N, is an    integer from 0 to 4;    -   from among these, preference is given to compounds (also in the        form of their salts) of the type of the        acylsulphamoylbenzamides, for example of the formula (S-VI)        below, which are known, for example, from WO 99/16744,

-   -   for example those in which    -   R_(E) ¹=cyclopropyl and R_(E) ⁵=2-OMe (“cyprosulphamide”, S3-1),    -   R_(E) ¹=cyclopropyl and R_(E) ⁵=5-Cl-2-OMe (S3-2), R_(E) ¹=ethyl        and R_(E) ⁵=2-OMe (S3-3),    -   R_(E) ¹=isopropyl and R_(E) ⁵=5-Cl-2-OMe (S3-4) and    -   R_(E) ¹=isopropyl and R_(E) ⁵=2-OMe (S3-5);        F) compounds of the type of the N-acylsulphamoylphenylureas of        the formula (S-VII), which are known, for example, from        EP-A-365484

in which

-   A is a radical from the group consisting of

-   R_(F) ¹ and R_(F) ² independently of one another are hydrogen,    (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl, (C₃-C₆)-alkenyl, (C₃-C₆)-alkynyl,

-   -   or (C₁-C₄)Alkoxy substituted by

-   -   or (C₁-C₄)Alkoxy, or

-   R_(F) ¹ and R_(F) ² together are a (C₄-C₆)-alkylene bridge and a    (C₄-C₆)-alkylene bridge interrupted by oxygen, sulphur, SO, SO₂, NH    or —N(C₁-C₄-alkyl)-,

-   R_(F) ³ is hydrogen or (C₁-C₄)-alkyl,

-   R_(F) ⁴ and R_(F) ⁵ independently of one another are hydrogen,    halogen, cyano, nitro, trifluoromethyl, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    —COOR^(j), —CONR^(k)R^(m), —COR^(n), —SO₂NR^(k)R^(m) or    —OSO₂—C₁-C₄-alkyl, or R^(a) and R^(b) together are a    (C₃-C₄)-alkylene bridge which may be substituted by halogen or    C₁-C₄-alkyl, or a (C₃-C₄)-alkenylene bridge which may be substituted    by halogen or (C₁-C₄)-alkyl, or a C₄-alkadienylene bridge which may    be substituted by halogen or (C₁-C₄)-alkyl, and

-   R^(g) and R^(h) independently of one another are hydrogen, halogen,    C₁-C₄-alkyl, trifluoromethyl, methoxy, methylthio or —COOR^(j),    where

-   R^(c) is hydrogen, halogen, (C₁-C₄)-alkyl or methoxy,

-   R^(d) is hydrogen, halogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl,    —COOR^(j) or —CONR^(k)R^(m),

-   R^(e) is hydrogen, halogen, C₁-C₄-alkyl, —COOR^(j), trifluoromethyl    or methoxy, or R^(d) and R^(e) together are a (C₃-C₄)-alkylene    bridge,

-   R^(f) is hydrogen, halogen or (C₁-C₄)-alkyl,

-   R^(X) and R^(Y) independently of one another are hydrogen, halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, —COOR⁴,    trifluoromethyl, nitro or cyano,

-   R^(j), R^(k) and R^(m) independently of one another are hydrogen or    (C₁-C₄)-alkyl,

-   R^(k) and R^(m) together are a (C₄-C₆)-alkylene bridge and a    (C₄-C₆)-alkylene bridge interrupted by oxygen, NH or    —N(C₁-C₄-alkyl)-, and

-   R^(n) is (C₁-C₄)-alkyl, phenyl or phenyl substituted by halogen,    (C₁-C₄)-alkyl, methoxy, nitro or trifluoromethyl,

-   from among these, preference is given to:    -   1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea,    -   1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea,    -   1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea,    -   1-[4-(N-naphthoylsulphamoyl)phenyl]-3,3-dimethylurea, including        the stereoisomers and agriculturally customary salts,

-   G) active compounds from the class of the hydroxyaromatics and the    aromatic-aliphatic carboxylic acid derivatives, for example    -   ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic        acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid,        4-fluorosalicyclic acid,        1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide,        2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described        in WO 2004084631, WO 2005015994, WO 2006007981, WO 2005016001;

-   H) active compounds from the class of the    1,2-dihydroquinoxalin-2-ones, for example

-   1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,    1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione,    1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one    hydrochloride,    1-(2-methylsulphonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,    as described in WO 2005112630,

-   I) active compounds which, in addition to herbicidal action against    harmful plants, also have safener action on crop plants such as    rice, for example “dimepiperate” or “MY-93” (see Pestic. Man.)    (=S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate), which is    known as safener for rice against damage caused by the herbicide    molinate,    -   “daimuron” or “SK 23” (see Pestic. Man.)        (=1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as        safener for rice against imazosulfuron herbicide damage,    -   “cumyluron”=“JC-940”        (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see        JP-A-60087254), which is known as a safener for rice against        damage by some herbicides,    -   “methoxyphenone” or “NK 049”        (=3,3′-dimethyl-4-methoxybenzophenone), which is known as        safener for rice against damage by some herbicides,    -   “CSB” (=1-bromo-4-(chloromethylsulphonyl)benzene) (CAS Reg. No.        54091-06-4 from Kumiai), which is known as safener for rice        against damage by some herbicides,

-   K) compounds of the formula (S-IX), as described in WO-A-1998/38856,

-   -   where the symbols and indices have the following meanings:    -   R_(K) ¹, R_(K) ² independently of one another are halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkylamino, di(C₁-C₄)-alkylamino, nitro;    -   A_(K) is COOR_(K) ³ or COOR_(K) ⁴    -   R_(K) ³, R_(K) ⁴ independently of one another are hydrogen,        (C₁-C₄)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₄)-alkynyl, cyanoalkyl,        (C₁-C₄)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl,        pyridinylalkyl and alkylammonium,    -   n_(K) ¹ is 0 or 1 and    -   n_(K) ², n_(K) ³ independently of one another are 0, 1 or 2;        preferably:        methyl (diphenylmethoxy)acetate (CAS reg no: 41858-19-9),

-   L) compounds of the formula (S-X)    -   as described in WO A-98/27049

where the symbols and indices have the following meanings:

-   X_(L) is CH or N,-   n_(L) if X=N, is an integer from 0 to 4 and    -   if X=CH, is an integer from 0 to 5,-   R_(L) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, nitro, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl, optionally    substituted phenyl, optionally substituted phenoxy,-   R_(L) ² is hydrogen or (C₁-C₄)-alkyl-   R_(L) ³ is hydrogen, (C₁-C₈)-alkyl, (C₁-C₄)-alkenyl,    (C₁-C₄)-alkynyl, or aryl, where each of the aforementioned    carbon-containing radicals is unsubstituted or substituted by one or    more, preferably up to three identical or different radicals from    the group consisting of halogen and alkoxy; or salts thereof.-   M) Active compounds from the class of the    3-(5-tetrazolylcarbonyl)-2-quinolones, for example    -   1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone        (CAS Reg. No. 219479-18-2),        1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone        (CAS Reg. No.: 95855-00-8), as described in WO-A-1999000020,-   N) compounds of the formula (S-XI) or (S-XII)    -   as described in WO-A-2007023719 and WO-A-2007023764

-   -   in which

-   R_(N) ¹ is halogen, (C₁-C₄)-alkyl, methoxy, nitro, cyano, CF₃, OCF₃,

-   Y, Z independently of one another are O or S,

-   n_(N) is an integer from 0 to 4,

-   R_(N) ² is (C₁-C₁₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl,    aryl; benzyl, halobenzyl,

-   R_(N) ³ is hydrogen, (C₁-C₆)-alkyl;

-   O) one or more compounds from the group consisting of:    -   1,8-naphthalic anhydride,    -   O,O-diethyl S-2-ethylthioethyl phosphorodithioate (disulfoton),    -   4-chlorophenyl methylcarbamate (mephenate),    -   O,Odiethyl O-phenyl phosphorothioate (dietholate),    -   4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415,        CAS Reg. No.: 31541-57-8),    -   2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838,        CAS Reg. No.: 133993-74-5),    -   methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate        (from WOA98/13361; CAS Reg. No.: 205121-04-6),    -   cyanomethoxyimino(phenyl)acetonitrile (cyometrinil)    -   1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil),    -   4′-chloro-2,2,2-trifluoroacetophenone        0-1,3-dioxolan-2-ylmethyloxime (fluxofenim),    -   4,6-dichloro-2-phenylpyrimidine (fenclorim),    -   benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate        (flurazole),    -   2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),    -   including the stereoisomers possible in each case, and the salts        customary in agriculture.

The weight ratios of herbicide (mixture) to safener depend generally onthe herbicide application rate and the efficacy of the safener inquestion and may vary within wide limits, for example in the range from200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20.Analogously to the compounds (I) or mixtures thereof, the safeners canbe formulated with further herbicides/pesticides and be provided andemployed as a finished formulation or tankmix with the herbicides.

For application, the herbicide or herbicide/safener formulations presentin commercial form are, if appropriate, diluted in a customary manner,for example in the case of wettable powders, emulsifiable concentrates,dispersions and water-dispersible granules with water. Preparations inthe form of dusts, granules for soil application or granules forbroadcasting and sprayable solutions are usually not diluted furtherwith other inert substances prior to application.

The required application rate of the compounds of the formula (I) and/ortheir salts varies according to the external conditions such as, interalia, temperature, humidity and the type of herbicide used. It can varywithin wide limits. For the application as herbicide for controllingharmful plants, it is, for example, in the range of from 0.001 to 10.0kg/ha or more of active substance, preferably in the range of from 0.005to 5 kg/ha, in particular in the range of from 0.01 to 1 kg/ha, ofactive substance. This applies both to the pre-emergence and thepost-emergence application.

When used as plant growth regulator, for example as culm stabilizer forcrop plants like those mentioned above, preferably cereal plants, suchas wheat, barley, rye, triticale, millet, rice or corn, the applicationrate is, for example, in the range of from 0.001 to 2 kg/ha or more ofactive substance, preferably in the range of from 0.005 to 1 kg/ha, inparticular in the range of from 10 to 500 g/ha of active substance, veryparticularly from 20 to 250 g/ha of active substance. This applies bothto application by the pre-emergence method and the post-emergencemethod, the post-emergence treatment generally being preferred.

The application as culm stabilizer may take place at various stages ofthe growth of the plants. Preferred is, for example, the applicationafter the tillering phase, at the beginning of the longitudinal growth.

As an alternative, application as plant growth regulator is alsopossible by treating the seed, which includes various techniques fordressing and coating seed. Here, the application rate depends on theparticular techniques and can be determined in preliminary tests.

In an exemplary manner, some synthesis examples of compounds of thegeneral formula (I) are described below. In the examples, the amounts(including percentages) refer to the weight, unless especially statedotherwise.

The symbols “>” and “<” mean “greater than” and “smaller than”,respectively. The symbol “≧” means “greater than or equal to”, thesymbol “≦” means “smaller than or equal to”.

If, in the context of the description and the examples, the terms “R”and “S” are given for the absolute configuration on a center ofchirality of the stereoisomers of the formula (I), this RS nomenclaturefollows, unless defined differently, the Cahn-Ingold-Prelog rule.

(A) Synthesis Examples Example A1 erythro- and threo-Methyl4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate (Table 2,Examples erythro-Ibb1082 and threo-Ibb1082)

Under protective gas (Ar), 0.055 g (1.015 mmol) of potassiumtert-butoxide was added to 1.048 g (5.329 mmol) of methyl3-(4-chlorophenyl)acrylate and 1.000 g (5.075 mmol) of(5-bromopyridin-3-yl)acetonitrile in 8.0 ml of toluene. 3 ml ofdimethylformamide were added, and the mixture was stirred at 80° C. for8 h. The solvent was removed under reduced pressure and the residue wastaken up in dichloromethane and washed twice with in each case 25 ml ofwater. The combined organic phases were washed successively with 1Naqueous hydrochloric acid and with saturated aqueous sodium chloridesolution and dried over sodium sulphate. The solvent was removed underreduced pressure. Chromatography of the residue on silica gel (gradient:starting with ethyl acetate/heptane=5:95 over the course of 20 minutesincreased to ethyl acetate/heptane=30:70) gave, successively, 0.578 g(29% of theory) of threo-methyl4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate and 0.800 g(40% of theory) of erythro-methyl4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate. Theconfiguration was assigned by comparison of the chemical shifts of therespective CHCN doublets at 4.12 ppm and 4.49 ppm, respectively, in the¹H-NMR (CDCl₃). The lower-field signal was assigned to theerythro-diastereomer, analogously to the literature. ¹H-NMR in CDCl₃ seeTable 2.

Example A2 Methyl(3S,4S)-4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate(Table 2, Example threo-1-Ibb1082)

Preparative chromatography [(80 ml/min of n-heptane/2-propanol (70:30)]of the mixture, obtained in Example A1, of the racemic threo-methyl4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate on a chiralsolid phase [Chiralpak IC, 20 μm, (250×50)-mm column] gave 232.0 mg ofmethyl(3S,4S)-4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate[chemical purity>95% (NMR), isomeric purity>99% (chiral HPLC)], whichwas the first of the two stereoisomers to elute (retention time=12.17min). Specific rotation [α]: +61°. For ¹H-NMR in CDCl₃ and retentiontime in analytical HPLC: see Table 2.

Example A3 Methyl(3R,4R)-4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate(Table 2, Example threo-2-Ibb1082)

Preparative chromatography [(80 ml/min of n-heptane/2-propanol (70:30)]of the mixture, obtained in Example A1, of the racemic threo-methyl4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate on a chiralsolid phase [Chiralpak IC, 20 μm, (250×50)-mm column] gave 73.0 mg ofmethyl(3R,4R)-4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate[chemical purity>95% (NMR), isomeric purity>99% (chiral HPLC)], whichwas the last of the two stereoisomers to elute (retention time=20.01min). Specific rotation [α]: −61°. For ¹H-NMR in CDCl₃ and retentiontime in analytical HPLC: see Table 2.

The compounds, described in tables below, of the absolute configuration(3R,4R) are obtained according to or analogously to the examplesdescribed above.

Example A4 4-Cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoicacid (Table 2, Examples Iba1082)

Under protective gas (Ar), 3.0 ml of 2 molar aqueous sodium hydroxidesolution were added to 0.630 g (1.600 mmol) of methyl4-cyano-3-(2,6-difluorophenyl)-4-(3,4-difluorophenyl)butanoate (ExampleA1) in 160 ml of methanol, and the mixture was stirred at 25° C. for 2h. The methanol was removed under reduced pressure. The residue wasacidified with 2N aqueous hydrochloric acid (pH=3). Filtration anddrying of the residue under high vacuum at 40° C. gave 0.593 g (99.8% oftheory) of the title compound as a colourless solid[(erythro:threo=35:65, comparison of the doublets in the ¹H-NMR in CDCl₃at 4.14 (threo) and 4.50 ppm (erythro)]. ¹H-NMR in CDCl₃ see Table 2.

Example A5 Ethyl4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoate (Table 2,Examples Ibc1082)

Under protective gas (Ar), 0.121 g (0.632 mmol) ofN′-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDC), a spatula tip of4-dimethylaminopyridine (DMAP) and 0.061 g (1.317 mmol) of ethanol wereadded to 0.200 g (0.527 mmol) of4-cyano-4-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)butanoic acid (ExampleA4) in 4 ml of dichloromethane, and the mixture was stirred at 25° C.for 8 h. The solvent was removed under reduced pressure and the residuewas taken up in dichloromethane and washed twice with in each case 15 mlof water. The combined organic phases were dried over sodium sulphateand the solvent was removed under reduced pressure. Chromatography ofthe residue on silica gel (gradient: starting with ethylacetate/heptane=5:95 over the course of 20 minutes increased to ethylacetate/heptane=20:80) gave 0.143 g (67% of theory) of the titlecompound (erythro:threo=58:42). ¹H-NMR in CDCl₃ see Table 2.

The compounds described in the tables below are obtained according to oranalogously to the examples described above.

In the tables:

-   Ex.=Example number-   H=hydrogen (atom)-   Me=methyl-   Et=ethyl-   n-Pr=n-propyl-   i-Pr=isopropyl-   rt=retention time-   F, Cl, Br, I=fluorine, chlorine, bromine and iodine, respectively,    in accordance with the conventional chemical atom symbol-   CN=cyano-   NO₂=nitro-   MeO or OMe=methoxy-   CF₃=trifluoromethyl-   OCF₃=trifluoromethoxy-   OCF₂H=diflluoromethoxy-   CO₂Me=methoxycarbonyl (“methylester group”)

The position of a substituent at the phenyl ring, for example inposition 2, is stated as a prefix to the symbol or the abbreviation ofthe radical, for example

-   2-Cl=2-chloro-   2-F=2-fluoro

Numerations of the substituent positions for di- or trisubstitutedsubstitution patterns are analogously stated as a prefix, for example

-   3,4-Me₂=3,4-dimethyl (e.g. as substitution at the phenyl ring)-   3,5-F₂=3,5-difluoro (e.g. as substitution at the phenyl ring)-   3,4-F₂=3,4-difluoro (e.g. as substitution at the phenyl ring)

Other abbreviations are to be understood analogously to the examplesstated above.

-   “(R¹)_(m)=“H”=no substituent other than R³ present (m=0)-   “(R²)_(n)=“H”=unsubstituted cycle (n=0)

In addition, the customary chemical symbols and formulae apply, such as,for example, CH₂ for methylene or CF₃ for trifluoromethyl or OH forhydroxyl. Correspondingly, composite meanings are defined as composed ofthe abbreviations mentioned.

The retention times (“rt”) given for the compounds of Tables 2a-2f wereobtained by analytical HPLC of the compounds (I) on a chiral solidphase. At a concentration of 1 mg/ml, the compounds of the formula (I)were dissolved in dichloromethane p.a. and directly subjected to HPLC.The chromatographically purified compounds (I) have a stereochemicalpurity of ≧90%.

TABLE 1 Definitions of structural combinations of groups (R¹)_(m),(R²)_(n) and R³ for the tables of compounds of the general formula (I)according to the invention below No. (R¹)_(m) (R²)_(n) R³ 1 H 4-F F 2 H4-Cl F 3 H 4-Br F 4 H H F 5 H 4-Me F 6 H 4-CN F 7 H 4-NO₂ F 8 H 4-OMe F9 H 3-F F 10 H 3-Cl F 11 H 3-Br F 12 H 3-Me F 13 H 3-CN F 14 H 3-NO₂ F15 H 3-OMe F 16 H 2-F F 17 H 2-Cl F 18 H 2-Br F 19 H 2-Me F 20 H 2-CN F21 H 2-NO₂ F 22 H 2-OMe F 23 H 2,3-F₂ F 24 H 2,4-F₂ F 25 H 2,5-F₂ F 26 H2,6-F₂ F 27 H 3,4-F₂ F 28 H 3,5-F₂ F 29 H 2,3-Cl₂ F 30 H 2,4-Cl₂ F 31 H2,5-Cl₂ F 32 H 2,6-Cl₂ F 33 H 3,4-Cl₂ F 34 H 3,5-Cl₂ F 35 H 2-F, 3-Cl F36 H 2-F, 4-Cl F 37 H 2-F, 5-Cl F 38 H 2-F, 6-Cl F 39 H 2,6-F₂, 4-Cl F40 H 3-F, 4-Cl F 41 H 3-Cl, 5-F F 42 H 2-Cl, 5-F F 43 H 3-CN, 4-Cl F 44H 3-NO₂, 4-Cl F 45 H 2-F, 4-Br F 46 6-F 4-F F 47 6-F 4-Cl F 48 6-F 4-BrF 49 6-F H F 50 6-F 4-Me F 51 6-F 4-CN F 52 6-F 4-NO₂ F 53 6-F 4-OMe F54 6-F 3-F F 55 6-F 3-Cl F 56 6-F 3-Br F 57 6-F 3-Me F 58 6-F 3-CN F 596-F 3-NO₂ F 60 6-F 3-OMe F 61 6-F 2-F F 62 6-F 2-Cl F 63 6-F 2-Br F 646-F 2-Me F 65 6-F 2-CN F 66 6-F 2-NO₂ F 67 6-F 2-OMe F 68 6-F 2,3-F₂ F69 6-F 2,4-F₂ F 70 6-F 2,5-F₂ F 71 6-F 2,6-F₂ F 72 6-F 3,4-F₂ F 73 6-F3,5-F₂ F 74 6-F 2,3-Cl₂ F 75 6-F 2,4-Cl₂ F 76 6-F 2,5-Cl₂ F 77 6-F2,6-Cl₂ F 78 6-F 3,4-Cl₂ F 79 6-F 3,5-Cl₂ F 80 6-F 2-F, 3-Cl F 81 6-F2-F, 4-Cl F 82 6-F 2-F, 5-Cl F 83 6-F 2-F, 6-Cl F 84 6-F 2,6-F₂, 4-Cl F85 6-F 3-F, 4-Cl F 86 6-F 3-Cl, 5-F F 87 6-F 2-Cl, 5-F F 88 6-F 3-CN,4-Cl F 89 6-F 3-NO₂, 4-Cl F 90 6-F 2-F, 4-Br F 91 6-Cl 4-F F 92 6-Cl4-Cl F 93 6-Cl 4-Br F 94 6-Cl H F 95 6-Cl 4-Me F 96 6-Cl 4-CN F 97 6-Cl4-NO₂ F 98 6-Cl 4-OMe F 99 6-Cl 3-F F 100 6-Cl 3-Cl F 101 6-Cl 3-Br F102 6-Cl 3-Me F 103 6-Cl 3-CN F 104 6-Cl 3-NO₂ F 105 6-Cl 3-OMe F 1066-Cl 2-F F 107 6-Cl 2-Cl F 108 6-Cl 2-Br F 109 6-Cl 2-Me F 110 6-Cl 2-CNF 111 6-Cl 2-NO₂ F 112 6-Cl 2-OMe F 113 6-Cl 2,3-F₂ F 114 6-Cl 2,4-F₂ F115 6-Cl 2,5-F₂ F 116 6-Cl 2,6-F₂ F 117 6-Cl 3,4-F₂ F 118 6-Cl 3,5-F₂ F119 6-Cl 2,3-Cl₂ F 120 6-Cl 2,4-Cl₂ F 121 6-Cl 2,5-Cl₂ F 122 6-Cl2,6-Cl₂ F 123 6-Cl 3,4-Cl₂ F 124 6-Cl 3,5-Cl₂ F 125 6-Cl 2-F, 3-Cl F 1266-Cl 2-F, 4-Cl F 127 6-Cl 2-F, 5-Cl F 128 6-Cl 2-F, 6-Cl F 129 6-Cl2,6-F₂, 4-Cl F 130 6-Cl 3-F, 4-Cl F 131 6-Cl 3-Cl, 5-F F 132 6-Cl 2-Cl,5-F F 133 6-Cl 3-CN, 4-Cl F 134 6-Cl 3-NO₂, 4-Cl F 135 6-Cl 2-F, 4-Br F136 6-Br 4-F F 137 6-Br 4-Cl F 138 6-Br 4-Br F 139 6-Br H F 140 6-Br4-Me F 141 6-Br 4-CN F 142 6-Br 4-NO₂ F 143 6-Br 4-OMe F 144 6-Br 3-F F145 6-Br 3-Cl F 146 6-Br 3-Br F 147 6-Br 3-Me F 148 6-Br 3-CN F 149 6-Br3-NO₂ F 150 6-Br 3-OMe F 151 6-Br 2-F F 152 6-Br 2-Cl F 153 6-Br 2-Br F154 6-Br 2-Me F 155 6-Br 2-CN F 156 6-Br 2-NO₂ F 157 6-Br 2-OMe F 1586-Br 2,3-F₂ F 159 6-Br 2,4-F₂ F 160 6-Br 2,5-F₂ F 161 6-Br 2,6-F₂ F 1626-Br 3,4-F₂ F 163 6-Br 3,5-F₂ F 164 6-Br 2,3-Cl₂ F 165 6-Br 2,4-Cl₂ F166 6-Br 2,5-Cl₂ F 167 6-Br 2,6-Cl₂ F 168 6-Br 3,4-Cl₂ F 169 6-Br3,5-Cl₂ F 170 6-Br 2-F, 3-Cl F 171 6-Br 2-F, 4-Cl F 172 6-Br 2-F, 5-Cl F173 6-Br 2-F, 6-Cl F 174 6-Br 2,6-F₂, 4-Cl F 175 6-Br 3-F, 4-Cl F 1766-Br 3-Cl, 5-F F 177 6-Br 2-Cl, 5-F F 178 6-Br 3-CN, 4-Cl F 179 6-Br3-NO₂, 4-Cl F 180 6-Br 2-F, 4-Br F 181 6-CN 4-F F 182 6-CN 4-Cl F 1836-CN 4-Br F 184 6-CN H F 185 6-CN 4-Me F 186 6-CN 4-CN F 187 6-CN 4-NO₂F 188 6-CN 4-OMe F 189 6-CN 3-F F 190 6-CN 3-Cl F 191 6-CN 3-Br F 1926-CN 3-Me F 193 6-CN 3-CN F 194 6-CN 3-NO₂ F 195 6-CN 3-OMe F 196 6-CN2-F F 197 6-CN 2-Cl F 198 6-CN 2-Br F 199 6-CN 2-Me F 200 6-CN 2-CN F201 6-CN 2-NO₂ F 202 6-CN 2-OMe F 203 6-CN 2,3-F₂ F 204 6-CN 2,4-F₂ F205 6-CN 2,5-F₂ F 206 6-CN 2,6-F₂ F 207 6-CN 3,4-F₂ F 208 6-CN 3,5-F₂ F209 6-CN 2,3-Cl₂ F 210 6-CN 2,4-Cl₂ F 211 6-CN 2,5-Cl₂ F 212 6-CN2,6-Cl₂ F 213 6-CN 3,4-Cl₂ F 214 6-CN 3,5-Cl₂ F 215 6-CN 2-F, 3-Cl F 2166-CN 2-F, 4-Cl F 217 6-CN 2-F, 5-Cl F 218 6-CN 2-F, 6-Cl F 219 6-CN2,6-F₂, 4-Cl F 220 6-CN 3-F, 4-Cl F 221 6-CN 3-Cl, 5-F F 222 6-CN 2-Cl,5-F F 223 6-CN 3-CN, 4-Cl F 224 6-CN 3-NO₂, 4-Cl F 225 6-CN 2-F, 4-Br F226 6-Me 4-F F 227 6-Me 4-Cl F 228 6-Me 4-Br F 229 6-Me H F 230 6-Me4-Me F 231 6-Me 4-CN F 232 6-Me 4-NO₂ F 233 6-Me 4-OMe F 234 6-Me 3-F F235 6-Me 3-Cl F 236 6-Me 3-Br F 237 6-Me 3-Me F 238 6-Me 3-CN F 239 6-Me3-NO₂ F 240 6-Me 3-OMe F 241 6-Me 2-F F 242 6-Me 2-Cl F 243 6-Me 2-Br F244 6-Me 2-Me F 245 6-Me 2-CN F 246 6-Me 2-NO₂ F 247 6-Me 2-OMe F 2486-Me 2,3-F₂ F 249 6-Me 2,4-F₂ F 250 6-Me 2,5-F₂ F 251 6-Me 2,6-F₂ F 2526-Me 3,4-F₂ F 253 6-Me 3,5-F₂ F 254 6-Me 2,3-Cl₂ F 255 6-Me 2,4-Cl₂ F256 6-Me 2,5-Cl₂ F 257 6-Me 2,6-Cl₂ F 258 6-Me 3,4-Cl₂ F 259 6-Me3,5-Cl₂ F 260 6-Me 2-F, 3-Cl F 261 6-Me 2-F, 4-Cl F 262 6-Me 2-F, 5-Cl F263 6-Me 2-F, 6-Cl F 264 6-Me 2,6-F₂, 4-Cl F 265 6-Me 3-F, 4-Cl F 2666-Me 3-Cl, 5-F F 267 6-Me 2-Cl, 5-F F 268 6-Me 3-CN, 4-Cl F 269 6-Me3-NO₂, 4-Cl F 270 6-Me 2-F, 4-Br F 271 6-OMe 4-F F 272 6-OMe 4-Cl F 2736-OMe 4-Br F 274 6-OMe H F 275 6-OMe 4-Me F 276 6-OMe 4-CN F 277 6-OMe4-NO₂ F 278 6-OMe 4-OMe F 279 6-OMe 3-F F 280 6-OMe 3-Cl F 281 6-OMe3-Br F 282 6-OMe 3-Me F 283 6-OMe 3-CN F 284 6-OMe 3-NO₂ F 285 6-OMe3-OMe F 286 6-OMe 2-F F 287 6-OMe 2-Cl F 288 6-OMe 2-Br F 289 6-OMe 2-MeF 290 6-OMe 2-CN F 291 6-OMe 2-NO₂ F 292 6-OMe 2-OMe F 293 6-OMe 2,3-F₂F 294 6-OMe 2,4-F₂ F 295 6-OMe 2,5-F₂ F 296 6-OMe 2,6-F₂ F 297 6-OMe3,4-F₂ F 298 6-OMe 3,5-F₂ F 299 6-OMe 2,3-Cl₂ F 300 6-OMe 2,4-Cl₂ F 3016-OMe 2,5-Cl₂ F 302 6-OMe 2,6-Cl₂ F 303 6-OMe 3,4-Cl₂ F 304 6-OMe3,5-Cl₂ F 305 6-OMe 2-F, 3-Cl F 306 6-OMe 2-F, 4-Cl F 307 6-OMe 2-F,5-Cl F 308 6-OMe 2-F, 6-Cl F 309 6-OMe 2,6-F₂, 4-Cl F 310 6-OMe 3-F,4-Cl F 311 6-OMe 3-Cl, 5-F F 312 6-OMe 2-Cl, 5-F F 313 6-OMe 3-CN, 4-ClF 314 6-OMe 3-NO₂, 4-Cl F 315 6-OMe 2-F, 4-Br F 316 2-F 4-F F 317 2-F4-Cl F 318 2-F 4-Br F 319 2-F H F 320 2-F 4-Me F 321 2-F 4-CN F 322 2-F4-NO₂ F 323 2-F 4-OMe F 324 2-F 3-F F 325 2-F 3-Cl F 326 2-F 3-Br F 3272-F 3-Me F 328 2-F 3-CN F 329 2-F 3-NO₂ F 330 2-F 3-OMe F 331 2-F 2-F F332 2-F 2-Cl F 333 2-F 2-Br F 334 2-F 2-Me F 335 2-F 2-CN F 336 2-F2-NO₂ F 337 2-F 2-OMe F 338 2-F 2,3-F₂ F 339 2-F 2,4-F₂ F 340 2-F 2,5-F₂F 341 2-F 2,6-F₂ F 342 2-F 3,4-F₂ F 343 2-F 3,5-F₂ F 344 2-F 2,3-Cl₂ F345 2-F 2,4-Cl₂ F 346 2-F 2,5-Cl₂ F 347 2-F 2,6-Cl₂ F 348 2-F 3,4-Cl₂ F349 2-F 3,5-Cl₂ F 350 2-F 2-F, 3-Cl F 351 2-F 2-F, 4-Cl F 352 2-F 2-F,5-Cl F 353 2-F 2-F, 6-Cl F 354 2-F 2,6-F₂, 4-Cl F 355 2-F 3-F, 4-Cl F356 2-F 3-Cl, 5-F F 357 2-F 2-Cl, 5-F F 358 2-F 3-CN, 4-Cl F 359 2-F3-NO₂, 4-Cl F 360 2-F 2-F, 4-Br F 361 4-F 4-F F 362 4-F 4-Cl F 363 4-F4-Br F 364 4-F H F 365 4-F 4-Me F 366 4-F 4-CN F 367 4-F 4-NO₂ F 368 4-F4-OMe F 369 4-F 3-F F 370 4-F 3-Cl F 371 4-F 3-Br F 372 4-F 3-Me F 3734-F 3-CN F 374 4-F 3-NO₂ F 375 4-F 3-OMe F 376 4-F 2-F F 377 4-F 2-Cl F378 4-F 2-Br F 379 4-F 2-Me F 380 4-F 2-CN F 381 4-F 2-NO₂ F 382 4-F2-OMe F 383 4-F 2,3-F₂ F 384 4-F 2,4-F₂ F 385 4-F 2,5-F₂ F 386 4-F2,6-F₂ F 387 4-F 3,4-F₂ F 388 4-F 3,5-F₂ F 389 4-F 2,3-Cl₂ F 390 4-F2,4-Cl₂ F 391 4-F 2,5-Cl₂ F 392 4-F 2,6-Cl₂ F 393 4-F 3,4-Cl₂ F 394 4-F3,5-Cl₂ F 395 4-F 2-F, 3-Cl F 396 4-F 2-F, 4-Cl F 397 4-F 2-F, 5-Cl F398 4-F 2-F, 6-Cl F 399 4-F 2,6-F₂, 4-Cl F 400 4-F 3-F, 4-Cl F 401 4-F3-Cl, 5-F F 402 4-F 2-Cl, 5-F F 403 4-F 3-CN, 4-Cl F 404 4-F 3-NO₂, 4-ClF 405 4-F 2-F, 4-Br F 406 2-Cl 4-F F 407 2-Cl 4-Cl F 408 2-Cl 4-Br F 4092-Cl H F 410 2-Cl 4-Me F 411 2-Cl 4-CN F 412 2-Cl 4-NO₂ F 413 2-Cl 4-OMeF 414 2-Cl 3-F F 415 2-Cl 3-Cl F 416 2-Cl 3-Br F 417 2-Cl 3-Me F 4182-Cl 3-CN F 419 2-Cl 3-NO₂ F 420 2-Cl 3-OMe F 421 2-Cl 2-F F 422 2-Cl2-Cl F 423 2-Cl 2-Br F 424 2-Cl 2-Me F 425 2-Cl 2-CN F 426 2-Cl 2-NO₂ F427 2-Cl 2-OMe F 428 2-Cl 2,3-F₂ F 429 2-Cl 2,4-F₂ F 430 2-Cl 2,5-F₂ F431 2-Cl 2,6-F₂ F 432 2-Cl 3,4-F₂ F 433 2-Cl 3,5-F₂ F 434 2-Cl 2,3-Cl₂ F435 2-Cl 2,4-Cl₂ F 436 2-Cl 2,5-Cl₂ F 437 2-Cl 2,6-Cl₂ F 438 2-Cl3,4-Cl₂ F 439 2-Cl 3,5-Cl₂ F 440 2-Cl 2-F, 3-Cl F 441 2-Cl 2-F, 4-Cl F442 2-Cl 2-F, 5-Cl F 443 2-Cl 2-F, 6-Cl F 444 2-Cl 2,6-F₂, 4-Cl F 4452-Cl 3-F, 4-Cl F 446 2-Cl 3-Cl, 5-F F 447 2-Cl 2-Cl, 5-F F 448 2-Cl3-CN, 4-Cl F 449 2-Cl 3-NO₂, 4-Cl F 450 2-Cl 2-F, 4-Br F 451 4-Cl 4-F F452 4-Cl 4-Cl F 453 4-Cl 4-Br F 454 4-Cl H F 455 4-Cl 4-Me F 456 4-Cl4-CN F 457 4-Cl 4-NO₂ F 458 4-Cl 4-OMe F 459 4-Cl 3-F F 460 4-Cl 3-Cl F461 4-Cl 3-Br F 462 4-Cl 3-Me F 463 4-Cl 3-CN F 464 4-Cl 3-NO₂ F 4654-Cl 3-OMe F 466 4-Cl 2-F F 467 4-Cl 2-Cl F 468 4-Cl 2-Br F 469 4-Cl2-Me F 470 4-Cl 2-CN F 471 4-Cl 2-NO₂ F 472 4-Cl 2-OMe F 473 4-Cl 2,3-F₂F 474 4-Cl 2,4-F₂ F 475 4-Cl 2,5-F₂ F 476 4-Cl 2,6-F₂ F 477 4-Cl 3,4-F₂F 478 4-Cl 3,5-F₂ F 479 4-Cl 2,3-Cl₂ F 480 4-Cl 2,4-Cl₂ F 481 4-Cl2,5-Cl₂ F 482 4-Cl 2,6-Cl₂ F 483 4-Cl 3,4-Cl₂ F 484 4-Cl 3,5-Cl₂ F 4854-Cl 2-F, 3-Cl F 486 4-Cl 2-F, 4-Cl F 487 4-Cl 2-F, 5-Cl F 488 4-Cl 2-F,6-Cl F 489 4-Cl 2,6-F₂, 4-Cl F 490 4-Cl 3-F, 4-Cl F 491 4-Cl 3-Cl, 5-F F492 4-Cl 2-Cl, 5-F F 493 4-Cl 3-CN, 4-Cl F 494 4-Cl 3-NO₂, 4-Cl F 4954-Cl 2-F, 4-Br F 496 6-OCF₂H 4-F F 497 6-OCF₂H 4-Cl F 498 6-OCF₂H 4-Br F499 6-OCF₂H H F 500 6-OCF₂H 4-Me F 501 6-OCF₂H 4-CN F 502 6-OCF₂H 4-NO₂F 503 6-OCF₂H 4-OMe F 504 6-OCF₂H 3-F F 505 6-OCF₂H 3-Cl F 506 6-OCF₂H3-Br F 507 6-OCF₂H 3-Me F 508 6-OCF₂H 3-CN F 509 6-OCF₂H 3-NO₂ F 5106-OCF₂H 3-OMe F 511 6-OCF₂H 2-F F 512 6-OCF₂H 2-Cl F 513 6-OCF₂H 2-Br F514 6-OCF₂H 2-Me F 515 6-OCF₂H 2-CN F 516 6-OCF₂H 2-NO₂ F 517 6-OCF₂H2-OMe F 518 6-OCF₂H 2,3-F₂ F 519 6-OCF₂H 2,4-F₂ F 520 6-OCF₂H 2,5-F₂ F521 6-OCF₂H 2,6-F₂ F 522 6-OCF₂H 3,4-F₂ F 523 6-OCF₂H 3,5-F₂ F 5246-OCF₂H 2,3-Cl₂ F 525 6-OCF₂H 2,4-Cl₂ F 526 6-OCF₂H 2,5-Cl₂ F 5276-OCF₂H 2,6-Cl₂ F 528 6-OCF₂H 3,4-Cl₂ F 529 6-OCF₂H 3,5-Cl₂ F 5306-OCF₂H 2-F, 3-Cl F 531 6-OCF₂H 2-F, 4-Cl F 532 6-OCF₂H 2-F, 5-Cl F 5336-OCF₂H 2-F, 6-Cl F 534 6-OCF₂H 2,6-F₂, 4-Cl F 535 6-OCF₂H 3-F, 4-Cl F536 6-OCF₂H 3-Cl, 5-F F 537 6-OCF₂H 2-Cl, 5-F F 538 6-OCF₂H 3-CN, 4-Cl F539 6-OCF₂H 3-NO₂, 4-Cl F 540 6-OCF₂H 2-F, 4-Br F 541 H 4-F Cl 542 H4-Cl Cl 543 H 4-Br Cl 544 H H Cl 545 H 4-Me Cl 546 H 4-CN Cl 547 H 4-NO₂Cl 548 H 4-OMe Cl 549 H 3-F Cl 550 H 3-Cl Cl 551 H 3-Br Cl 552 H 3-Me Cl553 H 3-CN Cl 554 H 3-NO₂ Cl 555 H 3-OMe Cl 556 H 2-F Cl 557 H 2-Cl Cl558 H 2-Br Cl 559 H 2-Me Cl 560 H 2-CN Cl 561 H 2-NO₂ Cl 562 H 2-OMe Cl563 H 2,3-F₂ Cl 564 H 2,4-F₂ Cl 565 H 2,5-F₂ Cl 566 H 2,6-F₂ Cl 567 H3,4-F₂ Cl 568 H 3,5-F₂ Cl 569 H 2,3-Cl₂ Cl 570 H 2,4-Cl₂ Cl 571 H2,5-Cl₂ Cl 572 H 2,6-Cl₂ Cl 573 H 3,4-Cl₂ Cl 574 H 3,5-Cl₂ Cl 575 H 2-F,3-Cl Cl 576 H 2-F, 4-Cl Cl 577 H 2-F, 5-Cl Cl 578 H 2-F, 6-Cl Cl 579 H2,6-F₂, 4-Cl Cl 580 H 3-F, 4-Cl Cl 581 H 3-Cl, 5-F Cl 582 H 2-Cl, 5-F Cl583 H 3-CN, 4-Cl Cl 584 H 3-NO₂, 4-Cl Cl 585 H 2-F, 4-Br Cl 586 6-F 4-FCl 587 6-F 4-Cl Cl 588 6-F 4-Br Cl 589 6-F H Cl 590 6-F 4-Me Cl 591 6-F4-CN Cl 592 6-F 4-NO₂ Cl 593 6-F 4-OMe Cl 594 6-F 3-F Cl 595 6-F 3-Cl Cl596 6-F 3-Br Cl 597 6-F 3-Me Cl 598 6-F 3-CN Cl 599 6-F 3-NO₂ Cl 600 6-F3-OMe Cl 601 6-F 2-F Cl 602 6-F 2-Cl Cl 603 6-F 2-Br Cl 604 6-F 2-Me Cl605 6-F 2-CN Cl 606 6-F 2-NO₂ Cl 607 6-F 2-OMe Cl 608 6-F 2,3-F₂ Cl 6096-F 2,4-F₂ Cl 610 6-F 2,5-F₂ Cl 611 6-F 2,6-F₂ Cl 612 6-F 3,4-F₂ Cl 6136-F 3,5-F₂ Cl 614 6-F 2,3-Cl₂ Cl 615 6-F 2,4-Cl₂ Cl 616 6-F 2,5-Cl₂ Cl617 6-F 2,6-Cl₂ Cl 618 6-F 3,4-Cl₂ Cl 619 6-F 3,5-Cl₂ Cl 620 6-F 2-F,3-Cl Cl 621 6-F 2-F, 4-Cl Cl 622 6-F 2-F, 5-Cl Cl 623 6-F 2-F, 6-Cl Cl624 6-F 2,6-F₂, 4-Cl Cl 625 6-F 3-F, 4-Cl Cl 626 6-F 3-Cl, 5-F Cl 6276-F 2-Cl, 5-F Cl 628 6-F 3-CN, 4-Cl Cl 629 6-F 3-NO₂, 4-Cl Cl 630 6-F2-F, 4-Br Cl 631 6-Cl 4-F Cl 632 6-Cl 4-Cl Cl 633 6-Cl 4-Br Cl 634 6-ClH Cl 635 6-Cl 4-Me Cl 636 6-Cl 4-CN Cl 637 6-Cl 4-NO₂ Cl 638 6-Cl 4-OMeCl 639 6-Cl 3-F Cl 640 6-Cl 3-Cl Cl 641 6-Cl 3-Br Cl 642 6-Cl 3-Me Cl643 6-Cl 3-CN Cl 644 6-Cl 3-NO₂ Cl 645 6-Cl 3-OMe Cl 646 6-Cl 2-F Cl 6476-Cl 2-Cl Cl 648 6-Cl 2-Br Cl 649 6-Cl 2-Me Cl 650 6-Cl 2-CN Cl 651 6-Cl2-NO₂ Cl 652 6-Cl 2-OMe Cl 653 6-Cl 2,3-F₂ Cl 654 6-Cl 2,4-F₂ Cl 6556-Cl 2,5-F₂ Cl 656 6-Cl 2,6-F₂ Cl 657 6-Cl 3,4-F₂ Cl 658 6-Cl 3,5-F₂ Cl659 6-Cl 2,3-Cl₂ Cl 660 6-Cl 2,4-Cl₂ Cl 661 6-Cl 2,5-Cl₂ Cl 662 6-Cl2,6-Cl₂ Cl 663 6-Cl 3,4-Cl₂ Cl 664 6-Cl 3,5-Cl₂ Cl 665 6-Cl 2-F, 3-Cl Cl666 6-Cl 2-F, 4-Cl Cl 667 6-Cl 2-F, 5-Cl Cl 668 6-Cl 2-F, 6-Cl Cl 6696-Cl 2,6-F₂, 4-Cl Cl 670 6-Cl 3-F, 4-Cl Cl 671 6-Cl 3-Cl, 5-F Cl 6726-Cl 2-Cl, 5-F Cl 673 6-Cl 3-CN, 4-Cl Cl 674 6-Cl 3-NO₂, 4-Cl Cl 6756-Cl 2-F, 4-Br Cl 676 6-Br 4-F Cl 677 6-Br 4-Cl Cl 678 6-Br 4-Br Cl 6796-Br H Cl 680 6-Br 4-Me Cl 681 6-Br 4-CN Cl 682 6-Br 4-NO₂ Cl 683 6-Br4-OMe Cl 684 6-Br 3-F Cl 685 6-Br 3-Cl Cl 686 6-Br 3-Br Cl 687 6-Br 3-MeCl 688 6-Br 3-CN Cl 689 6-Br 3-NO₂ Cl 690 6-Br 3-OMe Cl 691 6-Br 2-F Cl692 6-Br 2-Cl Cl 693 6-Br 2-Br Cl 694 6-Br 2-Me Cl 695 6-Br 2-CN Cl 6966-Br 2-NO₂ Cl 697 6-Br 2-OMe Cl 698 6-Br 2,3-F₂ Cl 699 6-Br 2,4-F₂ Cl700 6-Br 2,5-F₂ Cl 701 6-Br 2,6-F₂ Cl 702 6-Br 3,4-F₂ Cl 703 6-Br 3,5-F₂Cl 704 6-Br 2,3-Cl₂ Cl 705 6-Br 2,4-Cl₂ Cl 706 6-Br 2,5-Cl₂ Cl 707 6-Br2,6-Cl₂ Cl 708 6-Br 3,4-Cl₂ Cl 709 6-Br 3,5-Cl₂ Cl 710 6-Br 2-F, 3-Cl Cl711 6-Br 2-F, 4-Cl Cl 712 6-Br 2-F, 5-Cl Cl 713 6-Br 2-F, 6-Cl Cl 7146-Br 2,6-F₂, 4-Cl Cl 715 6-Br 3-F, 4-Cl Cl 716 6-Br 3-Cl, 5-F Cl 7176-Br 2-Cl, 5-F Cl 718 6-Br 3-CN, 4-Cl Cl 719 6-Br 3-NO₂, 4-Cl Cl 7206-Br 2-F, 4-Br Cl 721 6-CN 4-F Cl 722 6-CN 4-Cl Cl 723 6-CN 4-Br Cl 7246-CN H Cl 725 6-CN 4-Me Cl 726 6-CN 4-CN Cl 727 6-CN 4-NO₂ Cl 728 6-CN4-OMe Cl 729 6-CN 3-F Cl 730 6-CN 3-Cl Cl 731 6-CN 3-Br Cl 732 6-CN 3-MeCl 733 6-CN 3-CN Cl 734 6-CN 3-NO₂ Cl 735 6-CN 3-OMe Cl 736 6-CN 2-F Cl737 6-CN 2-Cl Cl 738 6-CN 2-Br Cl 739 6-CN 2-Me Cl 740 6-CN 2-CN Cl 7416-CN 2-NO₂ Cl 742 6-CN 2-OMe Cl 743 6-CN 2,3-F₂ Cl 744 6-CN 2,4-F₂ Cl745 6-CN 2,5-F₂ Cl 746 6-CN 2,6-F₂ Cl 747 6-CN 3,4-F₂ Cl 748 6-CN 3,5-F₂Cl 749 6-CN 2,3-Cl₂ Cl 750 6-CN 2,4-Cl₂ Cl 751 6-CN 2,5-Cl₂ Cl 752 6-CN2,6-Cl₂ Cl 753 6-CN 3,4-Cl₂ Cl 754 6-CN 3,5-Cl₂ Cl 755 6-CN 2-F, 3-Cl Cl756 6-CN 2-F, 4-Cl Cl 757 6-CN 2-F, 5-Cl Cl 758 6-CN 2-F, 6-Cl Cl 7596-CN 2,6-F₂, 4-Cl Cl 760 6-CN 3-F, 4-Cl Cl 761 6-CN 3-Cl, 5-F Cl 7626-CN 2-Cl, 5-F Cl 763 6-CN 3-CN, 4-Cl Cl 764 6-CN 3-NO₂, 4-Cl Cl 7656-CN 2-F, 4-Br Cl 766 6-Me 4-F Cl 767 6-Me 4-Cl Cl 768 6-Me 4-Br Cl 7696-Me H Cl 770 6-Me 4-Me Cl 771 6-Me 4-CN Cl 772 6-Me 4-NO₂ Cl 773 6-Me4-OMe Cl 774 6-Me 3-F Cl 775 6-Me 3-Cl Cl 776 6-Me 3-Br Cl 777 6-Me 3-MeCl 778 6-Me 3-CN Cl 779 6-Me 3-NO₂ Cl 780 6-Me 3-OMe Cl 781 6-Me 2-F Cl782 6-Me 2-Cl Cl 783 6-Me 2-Br Cl 784 6-Me 2-Me Cl 785 6-Me 2-CN Cl 7866-Me 2-NO₂ Cl 787 6-Me 2-OMe Cl 788 6-Me 2,3-F₂ Cl 789 6-Me 2,4-F₂ Cl790 6-Me 2,5-F₂ Cl 791 6-Me 2,6-F₂ Cl 792 6-Me 3,4-F₂ Cl 793 6-Me 3,5-F₂Cl 794 6-Me 2,3-Cl₂ Cl 795 6-Me 2,4-Cl₂ Cl 796 6-Me 2,5-Cl₂ Cl 797 6-Me2,6-Cl₂ Cl 798 6-Me 3,4-Cl₂ Cl 799 6-Me 3,5-Cl₂ Cl 800 6-Me 2-F, 3-Cl Cl801 6-Me 2-F, 4-Cl Cl 802 6-Me 2-F, 5-Cl Cl 803 6-Me 2-F, 6-Cl Cl 8046-Me 2,6-F₂, 4-Cl Cl 805 6-Me 3-F, 4-Cl Cl 806 6-Me 3-Cl, 5-F Cl 8076-Me 2-Cl, 5-F Cl 808 6-Me 3-CN, 4-Cl Cl 809 6-Me 3-NO₂, 4-Cl Cl 8106-Me 2-F, 4-Br Cl 811 6-OMe 4-F Cl 812 6-OMe 4-Cl Cl 813 6-OMe 4-Br Cl814 6-OMe H Cl 815 6-OMe 4-Me Cl 816 6-OMe 4-CN Cl 817 6-OMe 4-NO₂ Cl818 6-OMe 4-OMe Cl 819 6-OMe 3-F Cl 820 6-OMe 3-Cl Cl 821 6-OMe 3-Br Cl822 6-OMe 3-Me Cl 823 6-OMe 3-CN Cl 824 6-OMe 3-NO₂ Cl 825 6-OMe 3-OMeCl 826 6-OMe 2-F Cl 827 6-OMe 2-Cl Cl 828 6-OMe 2-Br Cl 829 6-OMe 2-MeCl 830 6-OMe 2-CN Cl 831 6-OMe 2-NO₂ Cl 832 6-OMe 2-OMe Cl 833 6-OMe2,3-F₂ Cl 834 6-OMe 2,4-F₂ Cl 835 6-OMe 2,5-F₂ Cl 836 6-OMe 2,6-F₂ Cl837 6-OMe 3,4-F₂ Cl 838 6-OMe 3,5-F₂ Cl 839 6-OMe 2,3-Cl₂ Cl 840 6-OMe2,4-Cl₂ Cl 841 6-OMe 2,5-Cl₂ Cl 842 6-OMe 2,6-Cl₂ Cl 843 6-OMe 3,4-Cl₂Cl 844 6-OMe 3,5-Cl₂ Cl 845 6-OMe 2-F, 3-Cl Cl 846 6-OMe 2-F, 4-Cl Cl847 6-OMe 2-F, 5-Cl Cl 848 6-OMe 2-F, 6-Cl Cl 849 6-OMe 2,6-F₂, 4-Cl Cl850 6-OMe 3-F, 4-Cl Cl 851 6-OMe 3-Cl, 5-F Cl 852 6-OMe 2-Cl, 5-F Cl 8536-OMe 3-CN, 4-Cl Cl 854 6-OMe 3-NO₂, 4-Cl Cl 855 6-OMe 2-F, 4-Br Cl 8562-F 4-F Cl 857 2-F 4-Cl Cl 858 2-F 4-Br Cl 859 2-F H Cl 860 2-F 4-Me Cl861 2-F 4-CN Cl 862 2-F 4-NO₂ Cl 863 2-F 4-OMe Cl 864 2-F 3-F Cl 865 2-F3-Cl Cl 866 2-F 3-Br Cl 867 2-F 3-Me Cl 868 2-F 3-CN Cl 869 2-F 3-NO₂ Cl870 2-F 3-OMe Cl 871 2-F 2-F Cl 872 2-F 2-Cl Cl 873 2-F 2-Br Cl 874 2-F2-Me Cl 875 2-F 2-CN Cl 876 2-F 2-NO₂ Cl 877 2-F 2-OMe Cl 878 2-F 2,3-F₂Cl 879 2-F 2,4-F₂ Cl 880 2-F 2,5-F₂ Cl 881 2-F 2,6-F₂ Cl 882 2-F 3,4-F₂Cl 883 2-F 3,5-F₂ Cl 884 2-F 2,3-Cl₂ Cl 885 2-F 2,4-Cl₂ Cl 886 2-F2,5-Cl₂ Cl 887 2-F 2,6-Cl₂ Cl 888 2-F 3,4-Cl₂ Cl 889 2-F 3,5-Cl₂ Cl 8902-F 2-F, 3-Cl Cl 891 2-F 2-F, 4-Cl Cl 892 2-F 2-F, 5-Cl Cl 893 2-F 2-F,6-Cl Cl 894 2-F 2,6-F₂, 4-Cl Cl 895 2-F 3-F, 4-Cl Cl 896 2-F 3-Cl, 5-FCl 897 2-F 2-Cl, 5-F Cl 898 2-F 3-CN, 4-Cl Cl 899 2-F 3-NO₂, 4-Cl Cl 9002-F 2-F, 4-Br Cl 901 4-F 4-F Cl 902 4-F 4-Cl Cl 903 4-F 4-Br Cl 904 4-FH Cl 905 4-F 4-Me Cl 906 4-F 4-CN Cl 907 4-F 4-NO₂ Cl 908 4-F 4-OMe Cl909 4-F 3-F Cl 910 4-F 3-Cl Cl 911 4-F 3-Br Cl 912 4-F 3-Me Cl 913 4-F3-CN Cl 914 4-F 3-NO₂ Cl 915 4-F 3-OMe Cl 916 4-F 2-F Cl 917 4-F 2-Cl Cl918 4-F 2-Br Cl 919 4-F 2-Me Cl 920 4-F 2-CN Cl 921 4-F 2-NO₂ Cl 922 4-F2-OMe Cl 923 4-F 2,3-F₂ Cl 924 4-F 2,4-F₂ Cl 925 4-F 2,5-F₂ Cl 926 4-F2,6-F₂ Cl 927 4-F 3,4-F₂ Cl 928 4-F 3,5-F₂ Cl 929 4-F 2,3-Cl₂ Cl 930 4-F2,4-Cl₂ Cl 931 4-F 2,5-Cl₂ Cl 932 4-F 2,6-Cl₂ Cl 933 4-F 3,4-Cl₂ Cl 9344-F 3,5-Cl₂ Cl 935 4-F 2-F, 3-Cl Cl 936 4-F 2-F, 4-Cl Cl 937 4-F 2-F,5-Cl Cl 938 4-F 2-F, 6-Cl Cl 939 4-F 2,6-F₂, 4-Cl Cl 940 4-F 3-F, 4-ClCl 941 4-F 3-Cl, 5-F Cl 942 4-F 2-Cl, 5-F Cl 943 4-F 3-CN, 4-Cl Cl 9444-F 3-NO₂, 4-Cl Cl 945 4-F 2-F, 4-Br Cl 946 2-Cl 4-F Cl 947 2-Cl 4-Cl Cl948 2-Cl 4-Br Cl 949 2-Cl H Cl 950 2-Cl 4-Me Cl 951 2-Cl 4-CN Cl 9522-Cl 4-NO₂ Cl 953 2-Cl 4-OMe Cl 954 2-Cl 3-F Cl 955 2-Cl 3-Cl Cl 9562-Cl 3-Br Cl 957 2-Cl 3-Me Cl 958 2-Cl 3-CN Cl 959 2-Cl 3-NO₂ Cl 9602-Cl 3-OMe Cl 961 2-Cl 2-F Cl 962 2-Cl 2-Cl Cl 963 2-Cl 2-Br Cl 964 2-Cl2-Me Cl 965 2-Cl 2-CN Cl 966 2-Cl 2-NO₂ Cl 967 2-Cl 2-OMe Cl 968 2-Cl2,3-F₂ Cl 969 2-Cl 2,4-F₂ Cl 970 2-Cl 2,5-F₂ Cl 971 2-Cl 2,6-F₂ Cl 9722-Cl 3,4-F₂ Cl 973 2-Cl 3,5-F₂ Cl 974 2-Cl 2,3-Cl₂ Cl 975 2-Cl 2,4-Cl₂Cl 976 2-Cl 2,5-Cl₂ Cl 977 2-Cl 2,6-Cl₂ Cl 978 2-Cl 3,4-Cl₂ Cl 979 2-Cl3,5-Cl₂ Cl 980 2-Cl 2-F, 3-Cl Cl 981 2-Cl 2-F, 4-Cl Cl 982 2-Cl 2-F,5-Cl Cl 983 2-Cl 2-F, 6-Cl Cl 984 2-Cl 2,6-F₂, 4-Cl Cl 985 2-Cl 3-F,4-Cl Cl 986 2-Cl 3-Cl, 5-F Cl 987 2-Cl 2-Cl, 5-F Cl 988 2-Cl 3-CN, 4-ClCl 989 2-Cl 3-NO₂, 4-Cl Cl 990 2-Cl 2-F, 4-Br Cl 991 4-Cl 4-F Cl 9924-Cl 4-Cl Cl 993 4-Cl 4-Br Cl 994 4-Cl H Cl 995 4-Cl 4-Me Cl 996 4-Cl4-CN Cl 997 4-Cl 4-NO₂ Cl 998 4-Cl 4-OMe Cl 999 4-Cl 3-F Cl 1000 4-Cl3-Cl Cl 1001 4-Cl 3-Br Cl 1002 4-Cl 3-Me Cl 1003 4-Cl 3-CN Cl 1004 4-Cl3-NO₂ Cl 1005 4-Cl 3-OMe Cl 1006 4-Cl 2-F Cl 1007 4-Cl 2-Cl Cl 1008 4-Cl2-Br Cl 1009 4-Cl 2-Me Cl 1010 4-Cl 2-CN Cl 1011 4-Cl 2-NO₂ Cl 1012 4-Cl2-OMe Cl 1013 4-Cl 2,3-F₂ Cl 1014 4-Cl 2,4-F₂ Cl 1015 4-Cl 2,5-F₂ Cl1016 4-Cl 2,6-F₂ Cl 1017 4-Cl 3,4-F₂ Cl 1018 4-Cl 3,5-F₂ Cl 1019 4-Cl2,3-Cl₂ Cl 1020 4-Cl 2,4-Cl₂ Cl 1021 4-Cl 2,5-Cl₂ Cl 1022 4-Cl 2,6-Cl₂Cl 1023 4-Cl 3,4-Cl₂ Cl 1024 4-Cl 3,5-Cl₂ Cl 1025 4-Cl 2-F, 3-Cl Cl 10264-Cl 2-F, 4-Cl Cl 1027 4-Cl 2-F, 5-Cl Cl 1028 4-Cl 2-F, 6-Cl Cl 10294-Cl 2,6-F₂, 4-Cl Cl 1030 4-Cl 3-F, 4-Cl Cl 1031 4-Cl 3-Cl, 5-F Cl 10324-Cl 2-Cl, 5-F Cl 1033 4-Cl 3-CN, 4-Cl Cl 1034 4-Cl 3-NO₂, 4-Cl Cl 10354-Cl 2-F, 4-Br Cl 1036 6-OCF₂H 4-F Cl 1037 6-OCF₂H 4-Cl Cl 1038 6-OCF₂H4-Br Cl 1039 6-OCF₂H H Cl 1040 6-OCF₂H 4-Me Cl 1041 6-OCF₂H 4-CN Cl 10426-OCF₂H 4-NO₂ Cl 1043 6-OCF₂H 4-OMe Cl 1044 6-OCF₂H 3-F Cl 1045 6-OCF₂H3-Cl Cl 1046 6-OCF₂H 3-Br Cl 1047 6-OCF₂H 3-Me Cl 1048 6-OCF₂H 3-CN Cl1049 6-OCF₂H 3-NO₂ Cl 1050 6-OCF₂H 3-OMe Cl 1051 6-OCF₂H 2-F Cl 10526-OCF₂H 2-Cl Cl 1053 6-OCF₂H 2-Br Cl 1054 6-OCF₂H 2-Me Cl 1055 6-OCF₂H2-CN Cl 1056 6-OCF₂H 2-NO₂ Cl 1057 6-OCF₂H 2-OMe Cl 1058 6-OCF₂H 2,3-F₂Cl 1059 6-OCF₂H 2,4-F₂ Cl 1060 6-OCF₂H 2,5-F₂ Cl 1061 6-OCF₂H 2,6-F₂ Cl1062 6-OCF₂H 3,4-F₂ Cl 1063 6-OCF₂H 3,5-F₂ Cl 1064 6-OCF₂H 2,3-Cl₂ Cl1065 6-OCF₂H 2,4-Cl₂ Cl 1066 6-OCF₂H 2,5-Cl₂ Cl 1067 6-OCF₂H 2,6-Cl₂ Cl1068 6-OCF₂H 3,4-Cl₂ Cl 1069 6-OCF₂H 3,5-Cl₂ Cl 1070 6-OCF₂H 2-F, 3-ClCl 1071 6-OCF₂H 2-F, 4-Cl Cl 1072 6-OCF₂H 2-F, 5-Cl Cl 1073 6-OCF₂H 2-F,6-Cl Cl 1074 6-OCF₂H 2,6-F₂, 4-Cl Cl 1075 6-OCF₂H 3-F, 4-Cl Cl 10766-OCF₂H 3-Cl, 5-F Cl 1077 6-OCF₂H 2-Cl, 5-F Cl 1078 6-OCF₂H 3-CN, 4-ClCl 1079 6-OCF₂H 3-NO₂, 4-Cl Cl 1080 6-OCF₂H 2-F, 4-Br Cl 1081 H 4-F Br1082 H 4-Cl Br 1083 H 4-Br Br 1084 H H Br 1085 H 4-Me Br 1086 H 4-CN Br1087 H 4-NO₂ Br 1088 H 4-OMe Br 1089 H 3-F Br 1090 H 3-Cl Br 1091 H 3-BrBr 1092 H 3-Me Br 1093 H 3-CN Br 1094 H 3-NO₂ Br 1095 H 3-OMe Br 1096 H2-F Br 1097 H 2-Cl Br 1098 H 2-Br Br 1099 H 2-Me Br 1100 H 2-CN Br 1101H 2-NO₂ Br 1102 H 2-OMe Br 1103 H 2,3-F₂ Br 1104 H 2,4-F₂ Br 1105 H2,5-F₂ Br 1106 H 2,6-F₂ Br 1107 H 3,4-F₂ Br 1108 H 3,5-F₂ Br 1109 H2,3-Cl₂ Br 1110 H 2,4-Cl₂ Br 1111 H 2,5-Cl₂ Br 1112 H 2,6-Cl₂ Br 1113 H3,4-Cl₂ Br 1114 H 3,5-Cl₂ Br 1115 H 2-F, 3-Cl Br 1116 H 2-F, 4-Cl Br1117 H 2-F, 5-Cl Br 1118 H 2-F, 6-Cl Br 1119 H 2,6-F₂, 4-Cl Br 1120 H3-F, 4-Cl Br 1121 H 3-Cl, 5-F Br 1122 H 2-Cl, 5-F Br 1123 H 3-CN, 4-ClBr 1124 H 3-NO₂, 4-Cl Br 1125 H 2-F, 4-Br Br 1126 6-F 4-F Br 1127 6-F4-Cl Br 1128 6-F 4-Br Br 1129 6-F H Br 1130 6-F 4-Me Br 1131 6-F 4-CN Br1132 6-F 4-NO₂ Br 1133 6-F 4-OMe Br 1134 6-F 3-F Br 1135 6-F 3-Cl Br1136 6-F 3-Br Br 1137 6-F 3-Me Br 1138 6-F 3-CN Br 1139 6-F 3-NO₂ Br1140 6-F 3-OMe Br 1141 6-F 2-F Br 1142 6-F 2-Cl Br 1143 6-F 2-Br Br 11446-F 2-Me Br 1145 6-F 2-CN Br 1146 6-F 2-NO₂ Br 1147 6-F 2-OMe Br 11486-F 2,3-F₂ Br 1149 6-F 2,4-F₂ Br 1150 6-F 2,5-F₂ Br 1151 6-F 2,6-F₂ Br1152 6-F 3,4-F₂ Br 1153 6-F 3,5-F₂ Br 1154 6-F 2,3-Cl₂ Br 1155 6-F2,4-Cl₂ Br 1156 6-F 2,5-Cl₂ Br 1157 6-F 2,6-Cl₂ Br 1158 6-F 3,4-Cl₂ Br1159 6-F 3,5-Cl₂ Br 1160 6-F 2-F, 3-Cl Br 1161 6-F 2-F, 4-Cl Br 1162 6-F2-F, 5-Cl Br 1163 6-F 2-F, 6-Cl Br 1164 6-F 2,6-F₂, 4-Cl Br 1165 6-F3-F, 4-Cl Br 1166 6-F 3-Cl, 5-F Br 1167 6-F 2-Cl, 5-F Br 1168 6-F 3-CN,4-Cl Br 1169 6-F 3-NO₂, 4-Cl Br 1170 6-F 2-F, 4-Br Br 1171 6-Cl 4-F Br1172 6-Cl 4-Cl Br 1173 6-Cl 4-Br Br 1174 6-Cl H Br 1175 6-Cl 4-Me Br1176 6-Cl 4-CN Br 1177 6-Cl 4-NO₂ Br 1178 6-Cl 4-OMe Br 1179 6-Cl 3-F Br1180 6-Cl 3-Cl Br 1181 6-Cl 3-Br Br 1182 6-Cl 3-Me Br 1183 6-Cl 3-CN Br1184 6-Cl 3-NO₂ Br 1185 6-Cl 3-OMe Br 1186 6-Cl 2-F Br 1187 6-Cl 2-Cl Br1188 6-Cl 2-Br Br 1189 6-Cl 2-Me Br 1190 6-Cl 2-CN Br 1191 6-Cl 2-NO₂ Br1192 6-Cl 2-OMe Br 1193 6-Cl 2,3-F₂ Br 1194 6-Cl 2,4-F₂ Br 1195 6-Cl2,5-F₂ Br 1196 6-Cl 2,6-F₂ Br 1197 6-Cl 3,4-F₂ Br 1198 6-Cl 3,5-F₂ Br1199 6-Cl 2,3-Cl₂ Br 1200 6-Cl 2,4-Cl₂ Br 1201 6-Cl 2,5-Cl₂ Br 1202 6-Cl2,6-Cl₂ Br 1203 6-Cl 3,4-Cl₂ Br 1204 6-Cl 3,5-Cl₂ Br 1205 6-Cl 2-F, 3-ClBr 1206 6-Cl 2-F, 4-Cl Br 1207 6-Cl 2-F, 5-Cl Br 1208 6-Cl 2-F, 6-Cl Br1209 6-Cl 2,6-F₂, 4-Cl Br 1210 6-Cl 3-F, 4-Cl Br 1211 6-Cl 3-Cl, 5-F Br1212 6-Cl 2-Cl, 5-F Br 1213 6-Cl 3-CN, 4-Cl Br 1214 6-Cl 3-NO₂, 4-Cl Br1215 6-Cl 2-F, 4-Br Br 1216 6-Br 4-F Br 1217 6-Br 4-Cl Br 1218 6-Br 4-BrBr 1219 6-Br H Br 1220 6-Br 4-Me Br 1221 6-Br 4-CN Br 1222 6-Br 4-NO₂ Br1223 6-Br 4-OMe Br 1224 6-Br 3-F Br 1225 6-Br 3-Cl Br 1226 6-Br 3-Br Br1227 6-Br 3-Me Br 1228 6-Br 3-CN Br 1229 6-Br 3-NO₂ Br 1230 6-Br 3-OMeBr 1231 6-Br 2-F Br 1232 6-Br 2-Cl Br 1233 6-Br 2-Br Br 1234 6-Br 2-MeBr 1235 6-Br 2-CN Br 1236 6-Br 2-NO₂ Br 1237 6-Br 2-OMe Br 1238 6-Br2,3-F₂ Br 1239 6-Br 2,4-F₂ Br 1240 6-Br 2,5-F₂ Br 1241 6-Br 2,6-F₂ Br1242 6-Br 3,4-F₂ Br 1243 6-Br 3,5-F₂ Br 1244 6-Br 2,3-Cl₂ Br 1245 6-Br2,4-Cl₂ Br 1246 6-Br 2,5-Cl₂ Br 1247 6-Br 2,6-Cl₂ Br 1248 6-Br 3,4-Cl₂Br 1249 6-Br 3,5-Cl₂ Br 1250 6-Br 2-F, 3-Cl Br 1251 6-Br 2-F, 4-Cl Br1252 6-Br 2-F, 5-Cl Br 1253 6-Br 2-F, 6-Cl Br 1254 6-Br 2,6-F₂, 4-Cl Br1255 6-Br 3-F, 4-Cl Br 1256 6-Br 3-Cl, 5-F Br 1257 6-Br 2-Cl, 5-F Br1258 6-Br 3-CN, 4-Cl Br 1259 6-Br 3-NO₂, 4-Cl Br 1260 6-Br 2-F, 4-Br Br1261 6-CN 4-F Br 1262 6-CN 4-Cl Br 1263 6-CN 4-Br Br 1264 6-CN H Br 12656-CN 4-Me Br 1266 6-CN 4-CN Br 1267 6-CN 4-NO₂ Br 1268 6-CN 4-OMe Br1269 6-CN 3-F Br 1270 6-CN 3-Cl Br 1271 6-CN 3-Br Br 1272 6-CN 3-Me Br1273 6-CN 3-CN Br 1274 6-CN 3-NO₂ Br 1275 6-CN 3-OMe Br 1276 6-CN 2-F Br1277 6-CN 2-Cl Br 1278 6-CN 2-Br Br 1279 6-CN 2-Me Br 1280 6-CN 2-CN Br1281 6-CN 2-NO₂ Br 1282 6-CN 2-OMe Br 1283 6-CN 2,3-F₂ Br 1284 6-CN2,4-F₂ Br 1285 6-CN 2,5-F₂ Br 1286 6-CN 2,6-F₂ Br 1287 6-CN 3,4-F₂ Br1288 6-CN 3,5-F₂ Br 1289 6-CN 2,3-Cl₂ Br 1290 6-CN 2,4-Cl₂ Br 1291 6-CN2,5-Cl₂ Br 1292 6-CN 2,6-Cl₂ Br 1293 6-CN 3,4-Cl₂ Br 1294 6-CN 3,5-Cl₂Br 1295 6-CN 2-F, 3-Cl Br 1296 6-CN 2-F, 4-Cl Br 1297 6-CN 2-F, 5-Cl Br1298 6-CN 2-F, 6-Cl Br 1299 6-CN 2,6-F₂, 4-Cl Br 1300 6-CN 3-F, 4-Cl Br1301 6-CN 3-Cl, 5-F Br 1302 6-CN 2-Cl, 5-F Br 1303 6-CN 3-CN, 4-Cl Br1304 6-CN 3-NO₂, 4-Cl Br 1305 6-CN 2-F, 4-Br Br 1306 6-Me 4-F Br 13076-Me 4-Cl Br 1308 6-Me 4-Br Br 1309 6-Me H Br 1310 6-Me 4-Me Br 13116-Me 4-CN Br 1312 6-Me 4-NO₂ Br 1313 6-Me 4-OMe Br 1314 6-Me 3-F Br 13156-Me 3-Cl Br 1316 6-Me 3-Br Br 1317 6-Me 3-Me Br 1318 6-Me 3-CN Br 13196-Me 3-NO₂ Br 1320 6-Me 3-OMe Br 1321 6-Me 2-F Br 1322 6-Me 2-Cl Br 13236-Me 2-Br Br 1324 6-Me 2-Me Br 1325 6-Me 2-CN Br 1326 6-Me 2-NO₂ Br 13276-Me 2-OMe Br 1328 6-Me 2,3-F₂ Br 1329 6-Me 2,4-F₂ Br 1330 6-Me 2,5-F₂Br 1331 6-Me 2,6-F₂ Br 1332 6-Me 3,4-F₂ Br 1333 6-Me 3,5-F₂ Br 1334 6-Me2,3-Cl₂ Br 1335 6-Me 2,4-Cl₂ Br 1336 6-Me 2,5-Cl₂ Br 1337 6-Me 2,6-Cl₂Br 1338 6-Me 3,4-Cl₂ Br 1339 6-Me 3,5-Cl₂ Br 1340 6-Me 2-F, 3-Cl Br 13416-Me 2-F, 4-Cl Br 1342 6-Me 2-F, 5-Cl Br 1343 6-Me 2-F, 6-Cl Br 13446-Me 2,6-F₂, 4-Cl Br 1345 6-Me 3-F, 4-Cl Br 1346 6-Me 3-Cl, 5-F Br 13476-Me 2-Cl, 5-F Br 1348 6-Me 3-CN, 4-Cl Br 1349 6-Me 3-NO₂, 4-Cl Br 13506-Me 2-F, 4-Br Br 1351 6-OMe 4-F Br 1352 6-OMe 4-Cl Br 1353 6-OMe 4-BrBr 1354 6-OMe H Br 1355 6-OMe 4-Me Br 1356 6-OMe 4-CN Br 1357 6-OMe4-NO₂ Br 1358 6-OMe 4-OMe Br 1359 6-OMe 3-F Br 1360 6-OMe 3-Cl Br 13616-OMe 3-Br Br 1362 6-OMe 3-Me Br 1363 6-OMe 3-CN Br 1364 6-OMe 3-NO₂ Br1365 6-OMe 3-OMe Br 1366 6-OMe 2-F Br 1367 6-OMe 2-Cl Br 1368 6-OMe 2-BrBr 1369 6-OMe 2-Me Br 1370 6-OMe 2-CN Br 1371 6-OMe 2-NO₂ Br 1372 6-OMe2-OMe Br 1373 6-OMe 2,3-F₂ Br 1374 6-OMe 2,4-F₂ Br 1375 6-OMe 2,5-F₂ Br1376 6-OMe 2,6-F₂ Br 1377 6-OMe 3,4-F₂ Br 1378 6-OMe 3,5-F₂ Br 13796-OMe 2,3-Cl₂ Br 1380 6-OMe 2,4-Cl₂ Br 1381 6-OMe 2,5-Cl₂ Br 1382 6-OMe2,6-Cl₂ Br 1383 6-OMe 3,4-Cl₂ Br 1384 6-OMe 3,5-Cl₂ Br 1385 6-OMe 2-F,3-Cl Br 1386 6-OMe 2-F, 4-Cl Br 1387 6-OMe 2-F, 5-Cl Br 1388 6-OMe 2-F,6-Cl Br 1389 6-OMe 2,6-F₂, 4-Cl Br 1390 6-OMe 3-F, 4-Cl Br 1391 6-OMe3-Cl, 5-F Br 1392 6-OMe 2-Cl, 5-F Br 1393 6-OMe 3-CN, 4-Cl Br 1394 6-OMe3-NO₂, 4-Cl Br 1395 6-OMe 2-F, 4-Br Br 1396 2-F 4-F Br 1397 2-F 4-Cl Br1398 2-F 4-Br Br 1399 2-F H Br 1400 2-F 4-Me Br 1401 2-F 4-CN Br 14022-F 4-NO₂ Br 1403 2-F 4-OMe Br 1404 2-F 3-F Br 1405 2-F 3-Cl Br 1406 2-F3-Br Br 1407 2-F 3-Me Br 1408 2-F 3-CN Br 1409 2-F 3-NO₂ Br 1410 2-F3-OMe Br 1411 2-F 2-F Br 1412 2-F 2-Cl Br 1413 2-F 2-Br Br 1414 2-F 2-MeBr 1415 2-F 2-CN Br 1416 2-F 2-NO₂ Br 1417 2-F 2-OMe Br 1418 2-F 2,3-F₂Br 1419 2-F 2,4-F₂ Br 1420 2-F 2,5-F₂ Br 1421 2-F 2,6-F₂ Br 1422 2-F3,4-F₂ Br 1423 2-F 3,5-F₂ Br 1424 2-F 2,3-Cl₂ Br 1425 2-F 2,4-Cl₂ Br1426 2-F 2,5-Cl₂ Br 1427 2-F 2,6-Cl₂ Br 1428 2-F 3,4-Cl₂ Br 1429 2-F3,5-Cl₂ Br 1430 2-F 2-F, 3-Cl Br 1431 2-F 2-F, 4-Cl Br 1432 2-F 2-F,5-Cl Br 1433 2-F 2-F, 6-Cl Br 1434 2-F 2,6-F₂, 4-Cl Br 1435 2-F 3-F,4-Cl Br 1436 2-F 3-Cl, 5-F Br 1437 2-F 2-Cl, 5-F Br 1438 2-F 3-CN, 4-ClBr 1439 2-F 3-NO₂, 4-Cl Br 1440 2-F 2-F, 4-Br Br 1441 4-F 4-F Br 14424-F 4-Cl Br 1443 4-F 4-Br Br 1444 4-F H Br 1445 4-F 4-Me Br 1446 4-F4-CN Br 1447 4-F 4-NO₂ Br 1448 4-F 4-OMe Br 1449 4-F 3-F Br 1450 4-F3-Cl Br 1451 4-F 3-Br Br 1452 4-F 3-Me Br 1453 4-F 3-CN Br 1454 4-F3-NO₂ Br 1455 4-F 3-OMe Br 1456 4-F 2-F Br 1457 4-F 2-Cl Br 1458 4-F2-Br Br 1459 4-F 2-Me Br 1460 4-F 2-CN Br 1461 4-F 2-NO₂ Br 1462 4-F2-OMe Br 1463 4-F 2,3-F₂ Br 1464 4-F 2,4-F₂ Br 1465 4-F 2,5-F₂ Br 14664-F 2,6-F₂ Br 1467 4-F 3,4-F₂ Br 1468 4-F 3,5-F₂ Br 1469 4-F 2,3-Cl₂ Br1470 4-F 2,4-Cl₂ Br 1471 4-F 2,5-Cl₂ Br 1472 4-F 2,6-Cl₂ Br 1473 4-F3,4-Cl₂ Br 1474 4-F 3,5-Cl₂ Br 1475 4-F 2-F, 3-Cl Br 1476 4-F 2-F, 4-ClBr 1477 4-F 2-F, 5-Cl Br 1478 4-F 2-F, 6-Cl Br 1479 4-F 2,6-F₂, 4-Cl Br1480 4-F 3-F, 4-Cl Br 1481 4-F 3-Cl, 5-F Br 1482 4-F 2-Cl, 5-F Br 14834-F 3-CN, 4-Cl Br 1484 4-F 3-NO₂, 4-Cl Br 1485 4-F 2-F, 4-Br Br 14862-Cl 4-F Br 1487 2-Cl 4-Cl Br 1488 2-Cl 4-Br Br 1489 2-Cl H Br 1490 2-Cl4-Me Br 1491 2-Cl 4-CN Br 1492 2-Cl 4-NO₂ Br 1493 2-Cl 4-OMe Br 14942-Cl 3-F Br 1495 2-Cl 3-Cl Br 1496 2-Cl 3-Br Br 1497 2-Cl 3-Me Br 14982-Cl 3-CN Br 1499 2-Cl 3-NO₂ Br 1500 2-Cl 3-OMe Br 1501 2-Cl 2-F Br 15022-Cl 2-Cl Br 1503 2-Cl 2-Br Br 1504 2-Cl 2-Me Br 1505 2-Cl 2-CN Br 15062-Cl 2-NO₂ Br 1507 2-Cl 2-OMe Br 1508 2-Cl 2,3-F₂ Br 1509 2-Cl 2,4-F₂ Br1510 2-Cl 2,5-F₂ Br 1511 2-Cl 2,6-F₂ Br 1512 2-Cl 3,4-F₂ Br 1513 2-Cl3,5-F₂ Br 1514 2-Cl 2,3-Cl₂ Br 1515 2-Cl 2,4-Cl₂ Br 1516 2-Cl 2,5-Cl₂ Br1517 2-Cl 2,6-Cl₂ Br 1518 2-Cl 3,4-Cl₂ Br 1519 2-Cl 3,5-Cl₂ Br 1520 2-Cl2-F, 3-Cl Br 1521 2-Cl 2-F, 4-Cl Br 1522 2-Cl 2-F, 5-Cl Br 1523 2-Cl2-F, 6-Cl Br 1524 2-Cl 2,6-F₂, 4-Cl Br 1525 2-Cl 3-F, 4-Cl Br 1526 2-Cl3-Cl, 5-F Br 1527 2-Cl 2-Cl, 5-F Br 1528 2-Cl 3-CN, 4-Cl Br 1529 2-Cl3-NO₂, 4-Cl Br 1530 2-Cl 2-F, 4-Br Br 1531 4-Cl 4-F Br 1532 4-Cl 4-Cl Br1533 4-Cl 4-Br Br 1534 4-Cl H Br 1535 4-Cl 4-Me Br 1536 4-Cl 4-CN Br1537 4-Cl 4-NO₂ Br 1538 4-Cl 4-OMe Br 1539 4-Cl 3-F Br 1540 4-Cl 3-Cl Br1541 4-Cl 3-Br Br 1542 4-Cl 3-Me Br 1543 4-Cl 3-CN Br 1544 4-Cl 3-NO₂ Br1545 4-Cl 3-OMe Br 1546 4-Cl 2-F Br 1547 4-Cl 2-Cl Br 1548 4-Cl 2-Br Br1549 4-Cl 2-Me Br 1550 4-Cl 2-CN Br 1551 4-Cl 2-NO₂ Br 1552 4-Cl 2-OMeBr 1553 4-Cl 2,3-F₂ Br 1554 4-Cl 2,4-F₂ Br 1555 4-Cl 2,5-F₂ Br 1556 4-Cl2,6-F₂ Br 1557 4-Cl 3,4-F₂ Br 1558 4-Cl 3,5-F₂ Br 1559 4-Cl 2,3-Cl₂ Br1560 4-Cl 2,4-Cl₂ Br 1561 4-Cl 2,5-Cl₂ Br 1562 4-Cl 2,6-Cl₂ Br 1563 4-Cl3,4-Cl₂ Br 1564 4-Cl 3,5-Cl₂ Br 1565 4-Cl 2-F, 3-Cl Br 1566 4-Cl 2-F,4-Cl Br 1567 4-Cl 2-F, 5-Cl Br 1568 4-Cl 2-F, 6-Cl Br 1569 4-Cl 2,6-F₂,4-Cl Br 1570 4-Cl 3-F, 4-Cl Br 1571 4-Cl 3-Cl, 5-F Br 1572 4-Cl 2-Cl,5-F Br 1573 4-Cl 3-CN, 4-Cl Br 1574 4-Cl 3-NO₂, 4-Cl Br 1575 4-Cl 2-F,4-Br Br 1576 6-OCF₂H 4-F Br 1577 6-OCF₂H 4-Cl Br 1578 6-OCF₂H 4-Br Br1579 6-OCF₂H H Br 1580 6-OCF₂H 4-Me Br 1581 6-OCF₂H 4-CN Br 1582 6-OCF₂H4-NO₂ Br 1583 6-OCF₂H 4-OMe Br 1584 6-OCF₂H 3-F Br 1585 6-OCF₂H 3-Cl Br1586 6-OCF₂H 3-Br Br 1587 6-OCF₂H 3-Me Br 1588 6-OCF₂H 3-CN Br 15896-OCF₂H 3-NO₂ Br 1590 6-OCF₂H 3-OMe Br 1591 6-OCF₂H 2-F Br 1592 6-OCF₂H2-Cl Br 1593 6-OCF₂H 2-Br Br 1594 6-OCF₂H 2-Me Br 1595 6-OCF₂H 2-CN Br1596 6-OCF₂H 2-NO₂ Br 1597 6-OCF₂H 2-OMe Br 1598 6-OCF₂H 2,3-F₂ Br 15996-OCF₂H 2,4-F₂ Br 1600 6-OCF₂H 2,5-F₂ Br 1601 6-OCF₂H 2,6-F₂ Br 16026-OCF₂H 3,4-F₂ Br 1603 6-OCF₂H 3,5-F₂ Br 1604 6-OCF₂H 2,3-Cl₂ Br 16056-OCF₂H 2,4-Cl₂ Br 1606 6-OCF₂H 2,5-Cl₂ Br 1607 6-OCF₂H 2,6-Cl₂ Br 16086-OCF₂H 3,4-Cl₂ Br 1609 6-OCF₂H 3,5-Cl₂ Br 1610 6-OCF₂H 2-F, 3-Cl Br1611 6-OCF₂H 2-F, 4-Cl Br 1612 6-OCF₂H 2-F, 5-Cl Br 1613 6-OCF₂H 2-F,6-Cl Br 1614 6-OCF₂H 2,6-F₂, 4-Cl Br 1615 6-OCF₂H 3-F, 4-Cl Br 16166-OCF₂H 3-Cl, 5-F Br 1617 6-OCF₂H 2-Cl, 5-F Br 1618 6-OCF₂H 3-CN, 4-ClBr 1619 6-OCF₂H 3-NO₂, 4-Cl Br 1620 6-OCF₂H 2-F, 4-Br Br 1621 H 4-F Me1622 H 4-Cl Me 1623 H 4-Br Me 1624 H H Me 1625 H 4-Me Me 1626 H 4-CN Me1627 H 4-NO₂ Me 1628 H 4-OMe Me 1629 H 3-F Me 1630 H 3-Cl Me 1631 H 3-BrMe 1632 H 3-Me Me 1633 H 3-CN Me 1634 H 3-NO₂ Me 1635 H 3-OMe Me 1636 H2-F Me 1637 H 2-Cl Me 1638 H 2-Br Me 1639 H 2-Me Me 1640 H 2-CN Me 1641H 2-NO₂ Me 1642 H 2-OMe Me 1643 H 2,3-F₂ Me 1644 H 2,4-F₂ Me 1645 H2,5-F₂ Me 1646 H 2,6-F₂ Me 1647 H 3,4-F₂ Me 1648 H 3,5-F₂ Me 1649 H2,3-Cl₂ Me 1650 H 2,4-Cl₂ Me 1651 H 2,5-Cl₂ Me 1652 H 2,6-Cl₂ Me 1653 H3,4-Cl₂ Me 1654 H 3,5-Cl₂ Me 1655 H 2-F, 3-Cl Me 1656 H 2-F, 4-Cl Me1657 H 2-F, 5-Cl Me 1658 H 2-F, 6-Cl Me 1659 H 2,6-F₂, 4-Cl Me 1660 H3-F, 4-Cl Me 1661 H 3-Cl, 5-F Me 1662 H 2-Cl, 5-F Me 1663 H 3-CN, 4-ClMe 1664 H 3-NO₂, 4-Cl Me 1665 H 2-F, 4-Br Me 1666 6-F 4-F Me 1667 6-F4-Cl Me 1668 6-F 4-Br Me 1669 6-F H Me 1670 6-F 4-Me Me 1671 6-F 4-CN Me1672 6-F 4-NO₂ Me 1673 6-F 4-OMe Me 1674 6-F 3-F Me 1675 6-F 3-Cl Me1676 6-F 3-Br Me 1677 6-F 3-Me Me 1678 6-F 3-CN Me 1679 6-F 3-NO₂ Me1680 6-F 3-OMe Me 1681 6-F 2-F Me 1682 6-F 2-Cl Me 1683 6-F 2-Br Me 16846-F 2-Me Me 1685 6-F 2-CN Me 1686 6-F 2-NO₂ Me 1687 6-F 2-OMe Me 16886-F 2,3-F₂ Me 1689 6-F 2,4-F₂ Me 1690 6-F 2,5-F₂ Me 1691 6-F 2,6-F₂ Me1692 6-F 3,4-F₂ Me 1693 6-F 3,5-F₂ Me 1694 6-F 2,3-Cl₂ Me 1695 6-F2,4-Cl₂ Me 1696 6-F 2,5-Cl₂ Me 1697 6-F 2,6-Cl₂ Me 1698 6-F 3,4-Cl₂ Me1699 6-F 3,5-Cl₂ Me 1700 6-F 2-F, 3-Cl Me 1701 6-F 2-F, 4-Cl Me 1702 6-F2-F, 5-Cl Me 1703 6-F 2-F, 6-Cl Me 1704 6-F 2,6-F₂, 4-Cl Me 1705 6-F3-F, 4-Cl Me 1706 6-F 3-Cl, 5-F Me 1707 6-F 2-Cl, 5-F Me 1708 6-F 3-CN,4-Cl Me 1709 6-F 3-NO₂, 4-Cl Me 1710 6-F 2-F, 4-Br Me 1711 6-Cl 4-F Me1712 6-Cl 4-Cl Me 1713 6-Cl 4-Br Me 1714 6-Cl H Me 1715 6-Cl 4-Me Me1716 6-Cl 4-CN Me 1717 6-Cl 4-NO₂ Me 1718 6-Cl 4-OMe Me 1719 6-Cl 3-F Me1720 6-Cl 3-Cl Me 1721 6-Cl 3-Br Me 1722 6-Cl 3-Me Me 1723 6-Cl 3-CN Me1724 6-Cl 3-NO₂ Me 1725 6-Cl 3-OMe Me 1726 6-Cl 2-F Me 1727 6-Cl 2-Cl Me1728 6-Cl 2-Br Me 1729 6-Cl 2-Me Me 1730 6-Cl 2-CN Me 1731 6-Cl 2-NO₂ Me1732 6-Cl 2-OMe Me 1733 6-Cl 2,3-F₂ Me 1734 6-Cl 2,4-F₂ Me 1735 6-Cl2,5-F₂ Me 1736 6-Cl 2,6-F₂ Me 1737 6-Cl 3,4-F₂ Me 1738 6-Cl 3,5-F₂ Me1739 6-Cl 2,3-Cl₂ Me 1740 6-Cl 2,4-Cl₂ Me 1741 6-Cl 2,5-Cl₂ Me 1742 6-Cl2,6-Cl₂ Me 1743 6-Cl 3,4-Cl₂ Me 1744 6-Cl 3,5-Cl₂ Me 1745 6-Cl 2-F, 3-ClMe 1746 6-Cl 2-F, 4-Cl Me 1747 6-Cl 2-F, 5-Cl Me 1748 6-Cl 2-F, 6-Cl Me1749 6-Cl 2,6-F₂, 4-Cl Me 1750 6-Cl 3-F, 4-Cl Me 1751 6-Cl 3-Cl, 5-F Me1752 6-Cl 2-Cl, 5-F Me 1753 6-Cl 3-CN, 4-Cl Me 1754 6-Cl 3-NO₂, 4-Cl Me1755 6-Cl 2-F, 4-Br Me 1756 6-Br 4-F Me 1757 6-Br 4-Cl Me 1758 6-Br 4-BrMe 1759 6-Br H Me 1760 6-Br 4-Me Me 1761 6-Br 4-CN Me 1762 6-Br 4-NO₂ Me1763 6-Br 4-OMe Me 1764 6-Br 3-F Me 1765 6-Br 3-Cl Me 1766 6-Br 3-Br Me1767 6-Br 3-Me Me 1768 6-Br 3-CN Me 1769 6-Br 3-NO₂ Me 1770 6-Br 3-OMeMe 1771 6-Br 2-F Me 1772 6-Br 2-Cl Me 1773 6-Br 2-Br Me 1774 6-Br 2-MeMe 1775 6-Br 2-CN Me 1776 6-Br 2-NO₂ Me 1777 6-Br 2-OMe Me 1778 6-Br2,3-F₂ Me 1779 6-Br 2,4-F₂ Me 1780 6-Br 2,5-F₂ Me 1781 6-Br 2,6-F₂ Me1782 6-Br 3,4-F₂ Me 1783 6-Br 3,5-F₂ Me 1784 6-Br 2,3-Cl₂ Me 1785 6-Br2,4-Cl₂ Me 1786 6-Br 2,5-Cl₂ Me 1787 6-Br 2,6-Cl₂ Me 1788 6-Br 3,4-Cl₂Me 1789 6-Br 3,5-Cl₂ Me 1790 6-Br 2-F, 3-Cl Me 1791 6-Br 2-F, 4-Cl Me1792 6-Br 2-F, 5-Cl Me 1793 6-Br 2-F, 6-Cl Me 1794 6-Br 2,6-F₂, 4-Cl Me1795 6-Br 3-F, 4-Cl Me 1796 6-Br 3-Cl, 5-F Me 1797 6-Br 2-Cl, 5-F Me1798 6-Br 3-CN, 4-Cl Me 1799 6-Br 3-NO₂, 4-Cl Me 1800 6-Br 2-F, 4-Br Me1801 6-CN 4-F Me 1802 6-CN 4-Cl Me 1803 6-CN 4-Br Me 1804 6-CN H Me 18056-CN 4-Me Me 1806 6-CN 4-CN Me 1807 6-CN 4-NO₂ Me 1808 6-CN 4-OMe Me1809 6-CN 3-F Me 1810 6-CN 3-Cl Me 1811 6-CN 3-Br Me 1812 6-CN 3-Me Me1813 6-CN 3-CN Me 1814 6-CN 3-NO₂ Me 1815 6-CN 3-OMe Me 1816 6-CN 2-F Me1817 6-CN 2-Cl Me 1818 6-CN 2-Br Me 1819 6-CN 2-Me Me 1820 6-CN 2-CN Me1821 6-CN 2-NO₂ Me 1822 6-CN 2-OMe Me 1823 6-CN 2,3-F₂ Me 1824 6-CN2,4-F₂ Me 1825 6-CN 2,5-F₂ Me 1826 6-CN 2,6-F₂ Me 1827 6-CN 3,4-F₂ Me1828 6-CN 3,5-F₂ Me 1829 6-CN 2,3-Cl₂ Me 1830 6-CN 2,4-Cl₂ Me 1831 6-CN2,5-Cl₂ Me 1832 6-CN 2,6-Cl₂ Me 1833 6-CN 3,4-Cl₂ Me 1834 6-CN 3,5-Cl₂Me 1835 6-CN 2-F, 3-Cl Me 1836 6-CN 2-F, 4-Cl Me 1837 6-CN 2-F, 5-Cl Me1838 6-CN 2-F, 6-Cl Me 1839 6-CN 2,6-F₂, 4-Cl Me 1840 6-CN 3-F, 4-Cl Me1841 6-CN 3-Cl, 5-F Me 1842 6-CN 2-Cl, 5-F Me 1843 6-CN 3-CN, 4-Cl Me1844 6-CN 3-NO₂, 4-Cl Me 1845 6-CN 2-F, 4-Br Me 1846 6-Me 4-F Me 18476-Me 4-Cl Me 1848 6-Me 4-Br Me 1849 6-Me H Me 1850 6-Me 4-Me Me 18516-Me 4-CN Me 1852 6-Me 4-NO₂ Me 1853 6-Me 4-OMe Me 1854 6-Me 3-F Me 18556-Me 3-Cl Me 1856 6-Me 3-Br Me 1857 6-Me 3-Me Me 1858 6-Me 3-CN Me 18596-Me 3-NO₂ Me 1860 6-Me 3-OMe Me 1861 6-Me 2-F Me 1862 6-Me 2-Cl Me 18636-Me 2-Br Me 1864 6-Me 2-Me Me 1865 6-Me 2-CN Me 1866 6-Me 2-NO₂ Me 18676-Me 2-OMe Me 1868 6-Me 2,3-F₂ Me 1869 6-Me 2,4-F₂ Me 1870 6-Me 2,5-F₂Me 1871 6-Me 2,6-F₂ Me 1872 6-Me 3,4-F₂ Me 1873 6-Me 3,5-F₂ Me 1874 6-Me2,3-Cl₂ Me 1875 6-Me 2,4-Cl₂ Me 1876 6-Me 2,5-Cl₂ Me 1877 6-Me 2,6-Cl₂Me 1878 6-Me 3,4-Cl₂ Me 1879 6-Me 3,5-Cl₂ Me 1880 6-Me 2-F, 3-Cl Me 18816-Me 2-F, 4-Cl Me 1882 6-Me 2-F, 5-Cl Me 1883 6-Me 2-F, 6-Cl Me 18846-Me 2,6-F₂, 4-Cl Me 1885 6-Me 3-F, 4-Cl Me 1886 6-Me 3-Cl, 5-F Me 18876-Me 2-Cl, 5-F Me 1888 6-Me 3-CN, 4-Cl Me 1889 6-Me 3-NO₂, 4-Cl Me 18906-Me 2-F, 4-Br Me 1891 6-OMe 4-F Me 1892 6-OMe 4-Cl Me 1893 6-OMe 4-BrMe 1894 6-OMe H Me 1895 6-OMe 4-Me Me 1896 6-OMe 4-CN Me 1897 6-OMe4-NO₂ Me 1898 6-OMe 4-OMe Me 1899 6-OMe 3-F Me 1900 6-OMe 3-Cl Me 19016-OMe 3-Br Me 1902 6-OMe 3-Me Me 1903 6-OMe 3-CN Me 1904 6-OMe 3-NO₂ Me1905 6-OMe 3-OMe Me 1906 6-OMe 2-F Me 1907 6-OMe 2-Cl Me 1908 6-OMe 2-BrMe 1909 6-OMe 2-Me Me 1910 6-OMe 2-CN Me 1911 6-OMe 2-NO₂ Me 1912 6-OMe2-OMe Me 1913 6-OMe 2,3-F₂ Me 1914 6-OMe 2,4-F₂ Me 1915 6-OMe 2,5-F₂ Me1916 6-OMe 2,6-F₂ Me 1917 6-OMe 3,4-F₂ Me 1918 6-OMe 3,5-F₂ Me 19196-OMe 2,3-Cl₂ Me 1920 6-OMe 2,4-Cl₂ Me 1921 6-OMe 2,5-Cl₂ Me 1922 6-OMe2,6-Cl₂ Me 1923 6-OMe 3,4-Cl₂ Me 1924 6-OMe 3,5-Cl₂ Me 1925 6-OMe 2-F,3-Cl Me 1926 6-OMe 2-F, 4-Cl Me 1927 6-OMe 2-F, 5-Cl Me 1928 6-OMe 2-F,6-Cl Me 1929 6-OMe 2,6-F₂, 4-Cl Me 1930 6-OMe 3-F, 4-Cl Me 1931 6-OMe3-Cl, 5-F Me 1932 6-OMe 2-Cl, 5-F Me 1933 6-OMe 3-CN, 4-Cl Me 1934 6-OMe3-NO₂, 4-Cl Me 1935 6-OMe 2-F, 4-Br Me 1936 2-F 4-F Me 1937 2-F 4-Cl Me1938 2-F 4-Br Me 1939 2-F H Me 1940 2-F 4-Me Me 1941 2-F 4-CN Me 19422-F 4-NO₂ Me 1943 2-F 4-OMe Me 1944 2-F 3-F Me 1945 2-F 3-Cl Me 1946 2-F3-Br Me 1947 2-F 3-Me Me 1948 2-F 3-CN Me 1949 2-F 3-NO₂ Me 1950 2-F3-OMe Me 1951 2-F 2-F Me 1952 2-F 2-Cl Me 1953 2-F 2-Br Me 1954 2-F 2-MeMe 1955 2-F 2-CN Me 1956 2-F 2-NO₂ Me 1957 2-F 2-OMe Me 1958 2-F 2,3-F₂Me 1959 2-F 2,4-F₂ Me 1960 2-F 2,5-F₂ Me 1961 2-F 2,6-F₂ Me 1962 2-F3,4-F₂ Me 1963 2-F 3,5-F₂ Me 1964 2-F 2,3-Cl₂ Me 1965 2-F 2,4-Cl₂ Me1966 2-F 2,5-Cl₂ Me 1967 2-F 2,6-Cl₂ Me 1968 2-F 3,4-Cl₂ Me 1969 2-F3,5-Cl₂ Me 1970 2-F 2-F, 3-Cl Me 1971 2-F 2-F, 4-Cl Me 1972 2-F 2-F,5-Cl Me 1973 2-F 2-F, 6-Cl Me 1974 2-F 2,6-F₂, 4-Cl Me 1975 2-F 3-F,4-Cl Me 1976 2-F 3-Cl, 5-F Me 1977 2-F 2-Cl, 5-F Me 1978 2-F 3-CN, 4-ClMe 1979 2-F 3-NO₂, 4-Cl Me 1980 2-F 2-F, 4-Br Me 1981 4-F 4-F Me 19824-F 4-Cl Me 1983 4-F 4-Br Me 1984 4-F H Me 1985 4-F 4-Me Me 1986 4-F4-CN Me 1987 4-F 4-NO₂ Me 1988 4-F 4-OMe Me 1989 4-F 3-F Me 1990 4-F3-Cl Me 1991 4-F 3-Br Me 1992 4-F 3-Me Me 1993 4-F 3-CN Me 1994 4-F3-NO₂ Me 1995 4-F 3-OMe Me 1996 4-F 2-F Me 1997 4-F 2-Cl Me 1998 4-F2-Br Me 1999 4-F 2-Me Me 2000 4-F 2-CN Me 2001 4-F 2-NO₂ Me 2002 4-F2-OMe Me 2003 4-F 2,3-F₂ Me 2004 4-F 2,4-F₂ Me 2005 4-F 2,5-F₂ Me 20064-F 2,6-F₂ Me 2007 4-F 3,4-F₂ Me 2008 4-F 3,5-F₂ Me 2009 4-F 2,3-Cl₂ Me2010 4-F 2,4-Cl₂ Me 2011 4-F 2,5-Cl₂ Me 2012 4-F 2,6-Cl₂ Me 2013 4-F3,4-Cl₂ Me 2014 4-F 3,5-Cl₂ Me 2015 4-F 2-F, 3-Cl Me 2016 4-F 2-F, 4-ClMe 2017 4-F 2-F, 5-Cl Me 2018 4-F 2-F, 6-Cl Me 2019 4-F 2,6-F₂, 4-Cl Me2020 4-F 3-F, 4-Cl Me 2021 4-F 3-Cl, 5-F Me 2022 4-F 2-Cl, 5-F Me 20234-F 3-CN, 4-Cl Me 2024 4-F 3-NO₂, 4-Cl Me 2025 4-F 2-F, 4-Br Me 20262-Cl 4-F Me 2027 2-Cl 4-Cl Me 2028 2-Cl 4-Br Me 2029 2-Cl H Me 2030 2-Cl4-Me Me 2031 2-Cl 4-CN Me 2032 2-Cl 4-NO₂ Me 2033 2-Cl 4-OMe Me 20342-Cl 3-F Me 2035 2-Cl 3-Cl Me 2036 2-Cl 3-Br Me 2037 2-Cl 3-Me Me 20382-Cl 3-CN Me 2039 2-Cl 3-NO₂ Me 2040 2-Cl 3-OMe Me 2041 2-Cl 2-F Me 20422-Cl 2-Cl Me 2043 2-Cl 2-Br Me 2044 2-Cl 2-Me Me 2045 2-Cl 2-CN Me 20462-Cl 2-NO₂ Me 2047 2-Cl 2-OMe Me 2048 2-Cl 2,3-F₂ Me 2049 2-Cl 2,4-F₂ Me2050 2-Cl 2,5-F₂ Me 2051 2-Cl 2,6-F₂ Me 2052 2-Cl 3,4-F₂ Me 2053 2-Cl3,5-F₂ Me 2054 2-Cl 2,3-Cl₂ Me 2055 2-Cl 2,4-Cl₂ Me 2056 2-Cl 2,5-Cl₂ Me2057 2-Cl 2,6-Cl₂ Me 2058 2-Cl 3,4-Cl₂ Me 2059 2-Cl 3,5-Cl₂ Me 2060 2-Cl2-F, 3-Cl Me 2061 2-Cl 2-F, 4-Cl Me 2062 2-Cl 2-F, 5-Cl Me 2063 2-Cl2-F, 6-Cl Me 2064 2-Cl 2,6-F₂, 4-Cl Me 2065 2-Cl 3-F, 4-Cl Me 2066 2-Cl3-Cl, 5-F Me 2067 2-Cl 2-Cl, 5-F Me 2068 2-Cl 3-CN, 4-Cl Me 2069 2-Cl3-NO₂, 4-Cl Me 2070 2-Cl 2-F, 4-Br Me 2071 4-Cl 4-F Me 2072 4-Cl 4-Cl Me2073 4-Cl 4-Br Me 2074 4-Cl H Me 2075 4-Cl 4-Me Me 2076 4-Cl 4-CN Me2077 4-Cl 4-NO₂ Me 2078 4-Cl 4-OMe Me 2079 4-Cl 3-F Me 2080 4-Cl 3-Cl Me2081 4-Cl 3-Br Me 2082 4-Cl 3-Me Me 2083 4-Cl 3-CN Me 2084 4-Cl 3-NO₂ Me2085 4-Cl 3-OMe Me 2086 4-Cl 2-F Me 2087 4-Cl 2-Cl Me 2088 4-Cl 2-Br Me2089 4-Cl 2-Me Me 2090 4-Cl 2-CN Me 2091 4-Cl 2-NO₂ Me 2092 4-Cl 2-OMeMe 2093 4-Cl 2,3-F₂ Me 2094 4-Cl 2,4-F₂ Me 2095 4-Cl 2,5-F₂ Me 2096 4-Cl2,6-F₂ Me 2097 4-Cl 3,4-F₂ Me 2098 4-Cl 3,5-F₂ Me 2099 4-Cl 2,3-Cl₂ Me2100 4-Cl 2,4-Cl₂ Me 2101 4-Cl 2,5-Cl₂ Me 2102 4-Cl 2,6-Cl₂ Me 2103 4-Cl3,4-Cl₂ Me 2104 4-Cl 3,5-Cl₂ Me 2105 4-Cl 2-F, 3-Cl Me 2106 4-Cl 2-F,4-Cl Me 2107 4-Cl 2-F, 5-Cl Me 2108 4-Cl 2-F, 6-Cl Me 2109 4-Cl 2,6-F₂,4-Cl Me 2110 4-Cl 3-F, 4-Cl Me 2111 4-Cl 3-Cl, 5-F Me 2112 4-Cl 2-Cl,5-F Me 2113 4-Cl 3-CN, 4-Cl Me 2114 4-Cl 3-NO₂, 4-Cl Me 2115 4-Cl 2-F,4-Br Me 2116 6-OCF₂H 4-F Me 2117 6-OCF₂H 4-Cl Me 2118 6-OCF₂H 4-Br Me2119 6-OCF₂H H Me 2120 6-OCF₂H 4-Me Me 2121 6-OCF₂H 4-CN Me 2122 6-OCF₂H4-NO₂ Me 2123 6-OCF₂H 4-OMe Me 2124 6-OCF₂H 3-F Me 2125 6-OCF₂H 3-Cl Me2126 6-OCF₂H 3-Br Me 2127 6-OCF₂H 3-Me Me 2128 6-OCF₂H 3-CN Me 21296-OCF₂H 3-NO₂ Me 2130 6-OCF₂H 3-OMe Me 2131 6-OCF₂H 2-F Me 2132 6-OCF₂H2-Cl Me 2133 6-OCF₂H 2-Br Me 2134 6-OCF₂H 2-Me Me 2135 6-OCF₂H 2-CN Me2136 6-OCF₂H 2-NO₂ Me 2137 6-OCF₂H 2-OMe Me 2138 6-OCF₂H 2,3-F₂ Me 21396-OCF₂H 2,4-F₂ Me 2140 6-OCF₂H 2,5-F₂ Me 2141 6-OCF₂H 2,6-F₂ Me 21426-OCF₂H 3,4-F₂ Me 2143 6-OCF₂H 3,5-F₂ Me 2144 6-OCF₂H 2,3-Cl₂ Me 21456-OCF₂H 2,4-Cl₂ Me 2146 6-OCF₂H 2,5-Cl₂ Me 2147 6-OCF₂H 2,6-Cl₂ Me 21486-OCF₂H 3,4-Cl₂ Me 2149 6-OCF₂H 3,5-Cl₂ Me 2150 6-OCF₂H 2-F, 3-Cl Me2151 6-OCF₂H 2-F, 4-Cl Me 2152 6-OCF₂H 2-F, 5-Cl Me 2153 6-OCF₂H 2-F,6-Cl Me 2154 6-OCF₂H 2,6-F₂, 4-Cl Me 2155 6-OCF₂H 3-F, 4-Cl Me 21566-OCF₂H 3-Cl, 5-F Me 2157 6-OCF₂H 2-Cl, 5-F Me 2158 6-OCF₂H 3-CN, 4-ClMe 2159 6-OCF₂H 3-NO₂, 4-Cl Me 2160 6-OCF₂H 2-F, 4-Br Me 2161 H 4-F CN2162 H 4-Cl CN 2163 H 4-Br CN 2164 H H CN 2165 H 4-Me CN 2166 H 4-CN CN2167 H 4-NO₂ CN 2168 H 4-OMe CN 2169 H 3-F CN 2170 H 3-Cl CN 2171 H 3-BrCN 2172 H 3-Me CN 2173 H 3-CN CN 2174 H 3-NO₂ CN 2175 H 3-OMe CN 2176 H2-F CN 2177 H 2-Cl CN 2178 H 2-Br CN 2179 H 2-Me CN 2180 H 2-CN CN 2181H 2-NO₂ CN 2182 H 2-OMe CN 2183 H 2,3-F₂ CN 2184 H 2,4-F₂ CN 2185 H2,5-F₂ CN 2186 H 2,6-F₂ CN 2187 H 3,4-F₂ CN 2188 H 3,5-F₂ CN 2189 H2,3-Cl₂ CN 2190 H 2,4-Cl₂ CN 2191 H 2,5-Cl₂ CN 2192 H 2,6-Cl₂ CN 2193 H3,4-Cl₂ CN 2194 H 3,5-Cl₂ CN 2195 H 2-F, 3-Cl CN 2196 H 2-F, 4-Cl CN2197 H 2-F, 5-Cl CN 2198 H 2-F, 6-Cl CN 2199 H 2,6-F₂, 4-Cl CN 2200 H3-F, 4-Cl CN 2201 H 3-Cl, 5-F CN 2202 H 2-Cl, 5-F CN 2203 H 3-CN, 4-ClCN 2204 H 3-NO₂, 4-Cl CN 2205 H 2-F, 4-Br CN 2206 6-F 4-F CN 2207 6-F4-Cl CN 2208 6-F 4-Br CN 2209 6-F H CN 2210 6-F 4-Me CN 2211 6-F 4-CN CN2212 6-F 4-NO₂ CN 2213 6-F 4-OMe CN 2214 6-F 3-F CN 2215 6-F 3-Cl CN2216 6-F 3-Br CN 2217 6-F 3-Me CN 2218 6-F 3-CN CN 2219 6-F 3-NO₂ CN2220 6-F 3-OMe CN 2221 6-F 2-F CN 2222 6-F 2-Cl CN 2223 6-F 2-Br CN 22246-F 2-Me CN 2225 6-F 2-CN CN 2226 6-F 2-NO₂ CN 2227 6-F 2-OMe CN 22286-F 2,3-F₂ CN 2229 6-F 2,4-F₂ CN 2230 6-F 2,5-F₂ CN 2231 6-F 2,6-F₂ CN2232 6-F 3,4-F₂ CN 2233 6-F 3,5-F₂ CN 2234 6-F 2,3-Cl₂ CN 2235 6-F2,4-Cl₂ CN 2236 6-F 2,5-Cl₂ CN 2237 6-F 2,6-Cl₂ CN 2238 6-F 3,4-Cl₂ CN2239 6-F 3,5-Cl₂ CN 2240 6-F 2-F, 3-Cl CN 2241 6-F 2-F, 4-Cl CN 2242 6-F2-F, 5-Cl CN 2243 6-F 2-F, 6-Cl CN 2244 6-F 2,6-F₂, 4-Cl CN 2245 6-F3-F, 4-Cl CN 2246 6-F 3-Cl, 5-F CN 2247 6-F 2-Cl, 5-F CN 2248 6-F 3-CN,4-Cl CN 2249 6-F 3-NO₂, 4-Cl CN 2250 6-F 2-F, 4-Br CN 2251 6-Cl 4-F CN2252 6-Cl 4-Cl CN 2253 6-Cl 4-Br CN 2254 6-Cl H CN 2255 6-Cl 4-Me CN2256 6-Cl 4-CN CN 2257 6-Cl 4-NO₂ CN 2258 6-Cl 4-OMe CN 2259 6-Cl 3-F CN2260 6-Cl 3-Cl CN 2261 6-Cl 3-Br CN 2262 6-Cl 3-Me CN 2263 6-Cl 3-CN CN2264 6-Cl 3-NO₂ CN 2265 6-Cl 3-OMe CN 2266 6-Cl 2-F CN 2267 6-Cl 2-Cl CN2268 6-Cl 2-Br CN 2269 6-Cl 2-Me CN 2270 6-Cl 2-CN CN 2271 6-Cl 2-NO₂ CN2272 6-Cl 2-OMe CN 2273 6-Cl 2,3-F₂ CN 2274 6-Cl 2,4-F₂ CN 2275 6-Cl2,5-F₂ CN 2276 6-Cl 2,6-F₂ CN 2277 6-Cl 3,4-F₂ CN 2278 6-Cl 3,5-F₂ CN2279 6-Cl 2,3-Cl₂ CN 2280 6-Cl 2,4-Cl₂ CN 2281 6-Cl 2,5-Cl₂ CN 2282 6-Cl2,6-Cl₂ CN 2283 6-Cl 3,4-Cl₂ CN 2284 6-Cl 3,5-Cl₂ CN 2285 6-Cl 2-F, 3-ClCN 2286 6-Cl 2-F, 4-Cl CN 2287 6-Cl 2-F, 5-Cl CN 2288 6-Cl 2-F, 6-Cl CN2289 6-Cl 2,6-F₂, 4-Cl CN 2290 6-Cl 3-F, 4-Cl CN 2291 6-Cl 3-Cl, 5-F CN2292 6-Cl 2-Cl, 5-F CN 2293 6-Cl 3-CN, 4-Cl CN 2294 6-Cl 3-NO₂, 4-Cl CN2295 6-Cl 2-F, 4-Br CN 2296 6-Br 4-F CN 2297 6-Br 4-Cl CN 2298 6-Br 4-BrCN 2299 6-Br H CN 2300 6-Br 4-Me CN 2301 6-Br 4-CN CN 2302 6-Br 4-NO₂ CN2303 6-Br 4-OMe CN 2304 6-Br 3-F CN 2305 6-Br 3-Cl CN 2306 6-Br 3-Br CN2307 6-Br 3-Me CN 2308 6-Br 3-CN CN 2309 6-Br 3-NO₂ CN 2310 6-Br 3-OMeCN 2311 6-Br 2-F CN 2312 6-Br 2-Cl CN 2313 6-Br 2-Br CN 2314 6-Br 2-MeCN 2315 6-Br 2-CN CN 2316 6-Br 2-NO₂ CN 2317 6-Br 2-OMe CN 2318 6-Br2,3-F₂ CN 2319 6-Br 2,4-F₂ CN 2320 6-Br 2,5-F₂ CN 2321 6-Br 2,6-F₂ CN2322 6-Br 3,4-F₂ CN 2323 6-Br 3,5-F₂ CN 2324 6-Br 2,3-Cl₂ CN 2325 6-Br2,4-Cl₂ CN 2326 6-Br 2,5-Cl₂ CN 2327 6-Br 2,6-Cl₂ CN 2328 6-Br 3,4-Cl₂CN 2329 6-Br 3,5-Cl₂ CN 2330 6-Br 2-F, 3-Cl CN 2331 6-Br 2-F, 4-Cl CN2332 6-Br 2-F, 5-Cl CN 2333 6-Br 2-F, 6-Cl CN 2334 6-Br 2,6-F₂, 4-Cl CN2335 6-Br 3-F, 4-Cl CN 2336 6-Br 3-Cl, 5-F CN 2337 6-Br 2-Cl, 5-F CN2338 6-Br 3-CN, 4-Cl CN 2339 6-Br 3-NO₂, 4-Cl CN 2340 6-Br 2-F, 4-Br CN2341 6-CN 4-F CN 2342 6-CN 4-Cl CN 2343 6-CN 4-Br CN 2344 6-CN H CN 23456-CN 4-Me CN 2346 6-CN 4-CN CN 2347 6-CN 4-NO₂ CN 2348 6-CN 4-OMe CN2349 6-CN 3-F CN 2350 6-CN 3-Cl CN 2351 6-CN 3-Br CN 2352 6-CN 3-Me CN2353 6-CN 3-CN CN 2354 6-CN 3-NO₂ CN 2355 6-CN 3-OMe CN 2356 6-CN 2-F CN2357 6-CN 2-Cl CN 2358 6-CN 2-Br CN 2359 6-CN 2-Me CN 2360 6-CN 2-CN CN2361 6-CN 2-NO₂ CN 2362 6-CN 2-OMe CN 2363 6-CN 2,3-F₂ CN 2364 6-CN2,4-F₂ CN 2365 6-CN 2,5-F₂ CN 2366 6-CN 2,6-F₂ CN 2367 6-CN 3,4-F₂ CN2368 6-CN 3,5-F₂ CN 2369 6-CN 2,3-Cl₂ CN 2370 6-CN 2,4-Cl₂ CN 2371 6-CN2,5-Cl₂ CN 2372 6-CN 2,6-Cl₂ CN 2373 6-CN 3,4-Cl₂ CN 2374 6-CN 3,5-Cl₂CN 2375 6-CN 2-F, 3-Cl CN 2376 6-CN 2-F, 4-Cl CN 2377 6-CN 2-F, 5-Cl CN2378 6-CN 2-F, 6-Cl CN 2379 6-CN 2,6-F₂, 4-Cl CN 2380 6-CN 3-F, 4-Cl CN2381 6-CN 3-Cl, 5-F CN 2382 6-CN 2-Cl, 5-F CN 2383 6-CN 3-CN, 4-Cl CN2384 6-CN 3-NO₂, 4-Cl CN 2385 6-CN 2-F, 4-Br CN 2386 6-Me 4-F CN 23876-Me 4-Cl CN 2388 6-Me 4-Br CN 2389 6-Me H CN 2390 6-Me 4-Me CN 23916-Me 4-CN CN 2392 6-Me 4-NO₂ CN 2393 6-Me 4-OMe CN 2394 6-Me 3-F CN 23956-Me 3-Cl CN 2396 6-Me 3-Br CN 2397 6-Me 3-Me CN 2398 6-Me 3-CN CN 23996-Me 3-NO₂ CN 2400 6-Me 3-OMe CN 2401 6-Me 2-F CN 2402 6-Me 2-Cl CN 24036-Me 2-Br CN 2404 6-Me 2-Me CN 2405 6-Me 2-CN CN 2406 6-Me 2-NO₂ CN 24076-Me 2-OMe CN 2408 6-Me 2,3-F₂ CN 2409 6-Me 2,4-F₂ CN 2410 6-Me 2,5-F₂CN 2411 6-Me 2,6-F₂ CN 2412 6-Me 3,4-F₂ CN 2413 6-Me 3,5-F₂ CN 2414 6-Me2,3-Cl₂ CN 2415 6-Me 2,4-Cl₂ CN 2416 6-Me 2,5-Cl₂ CN 2417 6-Me 2,6-Cl₂CN 2418 6-Me 3,4-Cl₂ CN 2419 6-Me 3,5-Cl₂ CN 2420 6-Me 2-F, 3-Cl CN 24216-Me 2-F, 4-Cl CN 2422 6-Me 2-F, 5-Cl CN 2423 6-Me 2-F, 6-Cl CN 24246-Me 2,6-F₂, 4-Cl CN 2425 6-Me 3-F, 4-Cl CN 2426 6-Me 3-Cl, 5-F CN 24276-Me 2-Cl, 5-F CN 2428 6-Me 3-CN, 4-Cl CN 2429 6-Me 3-NO₂, 4-Cl CN 24306-Me 2-F, 4-Br CN 2431 6-OMe 4-F CN 2432 6-OMe 4-Cl CN 2433 6-OMe 4-BrCN 2434 6-OMe H CN 2435 6-OMe 4-Me CN 2436 6-OMe 4-CN CN 2437 6-OMe4-NO₂ CN 2438 6-OMe 4-OMe CN 2439 6-OMe 3-F CN 2440 6-OMe 3-Cl CN 24416-OMe 3-Br CN 2442 6-OMe 3-Me CN 2443 6-OMe 3-CN CN 2444 6-OMe 3-NO₂ CN2445 6-OMe 3-OMe CN 2446 6-OMe 2-F CN 2447 6-OMe 2-Cl CN 2448 6-OMe 2-BrCN 2449 6-OMe 2-Me CN 2450 6-OMe 2-CN CN 2451 6-OMe 2-NO₂ CN 2452 6-OMe2-OMe CN 2453 6-OMe 2,3-F₂ CN 2454 6-OMe 2,4-F₂ CN 2455 6-OMe 2,5-F₂ CN2456 6-OMe 2,6-F₂ CN 2457 6-OMe 3,4-F₂ CN 2458 6-OMe 3,5-F₂ CN 24596-OMe 2,3-Cl₂ CN 2460 6-OMe 2,4-Cl₂ CN 2461 6-OMe 2,5-Cl₂ CN 2462 6-OMe2,6-Cl₂ CN 2463 6-OMe 3,4-Cl₂ CN 2464 6-OMe 3,5-Cl₂ CN 2465 6-OMe 2-F,3-Cl CN 2466 6-OMe 2-F, 4-Cl CN 2467 6-OMe 2-F, 5-Cl CN 2468 6-OMe 2-F,6-Cl CN 2469 6-OMe 2,6-F₂, 4-Cl CN 2470 6-OMe 3-F, 4-Cl CN 2471 6-OMe3-Cl, 5-F CN 2472 6-OMe 2-Cl, 5-F CN 2473 6-OMe 3-CN, 4-Cl CN 2474 6-OMe3-NO₂, 4-Cl CN 2475 6-OMe 2-F, 4-Br CN 2476 2-F 4-F CN 2477 2-F 4-Cl CN2478 2-F 4-Br CN 2479 2-F H CN 2480 2-F 4-Me CN 2481 2-F 4-CN CN 24822-F 4-NO₂ CN 2483 2-F 4-OMe CN 2484 2-F 3-F CN 2485 2-F 3-Cl CN 2486 2-F3-Br CN 2487 2-F 3-Me CN 2488 2-F 3-CN CN 2489 2-F 3-NO₂ CN 2490 2-F3-OMe CN 2491 2-F 2-F CN 2492 2-F 2-Cl CN 2493 2-F 2-Br CN 2494 2-F 2-MeCN 2495 2-F 2-CN CN 2496 2-F 2-NO₂ CN 2497 2-F 2-OMe CN 2498 2-F 2,3-F₂CN 2499 2-F 2,4-F₂ CN 2500 2-F 2,5-F₂ CN 2501 2-F 2,6-F₂ CN 2502 2-F3,4-F₂ CN 2503 2-F 3,5-F₂ CN 2504 2-F 2,3-Cl₂ CN 2505 2-F 2,4-Cl₂ CN2506 2-F 2,5-Cl₂ CN 2507 2-F 2,6-Cl₂ CN 2508 2-F 3,4-Cl₂ CN 2509 2-F3,5-Cl₂ CN 2510 2-F 2-F, 3-Cl CN 2511 2-F 2-F, 4-Cl CN 2512 2-F 2-F,5-Cl CN 2513 2-F 2-F, 6-Cl CN 2514 2-F 2,6-F₂, 4-Cl CN 2515 2-F 3-F,4-Cl CN 2516 2-F 3-Cl, 5-F CN 2517 2-F 2-Cl, 5-F CN 2518 2-F 3-CN, 4-ClCN 2519 2-F 3-NO₂, 4-Cl CN 2520 2-F 2-F, 4-Br CN 2521 4-F 4-F CN 25224-F 4-Cl CN 2523 4-F 4-Br CN 2524 4-F H CN 2525 4-F 4-Me CN 2526 4-F4-CN CN 2527 4-F 4-NO₂ CN 2528 4-F 4-OMe CN 2529 4-F 3-F CN 2530 4-F3-Cl CN 2531 4-F 3-Br CN 2532 4-F 3-Me CN 2533 4-F 3-CN CN 2534 4-F3-NO₂ CN 2535 4-F 3-OMe CN 2536 4-F 2-F CN 2537 4-F 2-Cl CN 2538 4-F2-Br CN 2539 4-F 2-Me CN 2540 4-F 2-CN CN 2541 4-F 2-NO₂ CN 2542 4-F2-OMe CN 2543 4-F 2,3-F₂ CN 2544 4-F 2,4-F₂ CN 2545 4-F 2,5-F₂ CN 25464-F 2,6-F₂ CN 2547 4-F 3,4-F₂ CN 2548 4-F 3,5-F₂ CN 2549 4-F 2,3-Cl₂ CN2550 4-F 2,4-Cl₂ CN 2551 4-F 2,5-Cl₂ CN 2552 4-F 2,6-Cl₂ CN 2553 4-F3,4-Cl₂ CN 2554 4-F 3,5-Cl₂ CN 2555 4-F 2-F, 3-Cl CN 2556 4-F 2-F, 4-ClCN 2557 4-F 2-F, 5-Cl CN 2558 4-F 2-F, 6-Cl CN 2559 4-F 2,6-F₂, 4-Cl CN2560 4-F 3-F, 4-Cl CN 2561 4-F 3-Cl, 5-F CN 2562 4-F 2-Cl, 5-F CN 25634-F 3-CN, 4-Cl CN 2564 4-F 3-NO₂, 4-Cl CN 2565 4-F 2-F, 4-Br CN 25662-Cl 4-F CN 2567 2-Cl 4-Cl CN 2568 2-Cl 4-Br CN 2569 2-Cl H CN 2570 2-Cl4-Me CN 2571 2-Cl 4-CN CN 2572 2-Cl 4-NO₂ CN 2573 2-Cl 4-OMe CN 25742-Cl 3-F CN 2575 2-Cl 3-Cl CN 2576 2-Cl 3-Br CN 2577 2-Cl 3-Me CN 25782-Cl 3-CN CN 2579 2-Cl 3-NO₂ CN 2580 2-Cl 3-OMe CN 2581 2-Cl 2-F CN 25822-Cl 2-Cl CN 2583 2-Cl 2-Br CN 2584 2-Cl 2-Me CN 2585 2-Cl 2-CN CN 25862-Cl 2-NO₂ CN 2587 2-Cl 2-OMe CN 2588 2-Cl 2,3-F₂ CN 2589 2-Cl 2,4-F₂ CN2590 2-Cl 2,5-F₂ CN 2591 2-Cl 2,6-F₂ CN 2592 2-Cl 3,4-F₂ CN 2593 2-Cl3,5-F₂ CN 2594 2-Cl 2,3-Cl₂ CN 2595 2-Cl 2,4-Cl₂ CN 2596 2-Cl 2,5-Cl₂ CN2597 2-Cl 2,6-Cl₂ CN 2598 2-Cl 3,4-Cl₂ CN 2599 2-Cl 3,5-Cl₂ CN 2600 2-Cl2-F, 3-Cl CN 2601 2-Cl 2-F, 4-Cl CN 2602 2-Cl 2-F, 5-Cl CN 2603 2-Cl2-F, 6-Cl CN 2604 2-Cl 2,6-F₂, 4-Cl CN 2605 2-Cl 3-F, 4-Cl CN 2606 2-Cl3-Cl, 5-F CN 2607 2-Cl 2-Cl, 5-F CN 2608 2-Cl 3-CN, 4-Cl CN 2609 2-Cl3-NO₂, 4-Cl CN 2610 2-Cl 2-F, 4-Br CN 2611 4-Cl 4-F CN 2612 4-Cl 4-Cl CN2613 4-Cl 4-Br CN 2614 4-Cl H CN 2615 4-Cl 4-Me CN 2616 4-Cl 4-CN CN2617 4-Cl 4-NO₂ CN 2618 4-Cl 4-OMe CN 2619 4-Cl 3-F CN 2620 4-Cl 3-Cl CN2621 4-Cl 3-Br CN 2622 4-Cl 3-Me CN 2623 4-Cl 3-CN CN 2624 4-Cl 3-NO₂ CN2625 4-Cl 3-OMe CN 2626 4-Cl 2-F CN 2627 4-Cl 2-Cl CN 2628 4-Cl 2-Br CN2629 4-Cl 2-Me CN 2630 4-Cl 2-CN CN 2631 4-Cl 2-NO₂ CN 2632 4-Cl 2-OMeCN 2633 4-Cl 2,3-F₂ CN 2634 4-Cl 2,4-F₂ CN 2635 4-Cl 2,5-F₂ CN 2636 4-Cl2,6-F₂ CN 2637 4-Cl 3,4-F₂ CN 2638 4-Cl 3,5-F₂ CN 2639 4-Cl 2,3-Cl₂ CN2640 4-Cl 2,4-Cl₂ CN 2641 4-Cl 2,5-Cl₂ CN 2642 4-Cl 2,6-Cl₂ CN 2643 4-Cl3,4-Cl₂ CN 2644 4-Cl 3,5-Cl₂ CN 2645 4-Cl 2-F, 3-Cl CN 2646 4-Cl 2-F,4-Cl CN 2647 4-Cl 2-F, 5-Cl CN 2648 4-Cl 2-F, 6-Cl CN 2649 4-Cl 2,6-F₂,4-Cl CN 2650 4-Cl 3-F, 4-Cl CN 2651 4-Cl 3-Cl, 5-F CN 2652 4-Cl 2-Cl,5-F CN 2653 4-Cl 3-CN, 4-Cl CN 2654 4-Cl 3-NO₂, 4-Cl CN 2655 4-Cl 2-F,4-Br CN 2656 6-OCF₂H 4-F CN 2657 6-OCF₂H 4-Cl CN 2658 6-OCF₂H 4-Br CN2659 6-OCF₂H H CN 2660 6-OCF₂H 4-Me CN 2661 6-OCF₂H 4-CN CN 2662 6-OCF₂H4-NO₂ CN 2663 6-OCF₂H 4-OMe CN 2664 6-OCF₂H 3-F CN 2665 6-OCF₂H 3-Cl CN2666 6-OCF₂H 3-Br CN 2667 6-OCF₂H 3-Me CN 2668 6-OCF₂H 3-CN CN 26696-OCF₂H 3-NO₂ CN 2670 6-OCF₂H 3-OMe CN 2671 6-OCF₂H 2-F CN 2672 6-OCF₂H2-Cl CN 2673 6-OCF₂H 2-Br CN 2674 6-OCF₂H 2-Me CN 2675 6-OCF₂H 2-CN CN2676 6-OCF₂H 2-NO₂ CN 2677 6-OCF₂H 2-OMe CN 2678 6-OCF₂H 2,3-F₂ CN 26796-OCF₂H 2,4-F₂ CN 2680 6-OCF₂H 2,5-F₂ CN 2681 6-OCF₂H 2,6-F₂ CN 26826-OCF₂H 3,4-F₂ CN 2683 6-OCF₂H 3,5-F₂ CN 2684 6-OCF₂H 2,3-Cl₂ CN 26856-OCF₂H 2,4-Cl₂ CN 2686 6-OCF₂H 2,5-Cl₂ CN 2687 6-OCF₂H 2,6-Cl₂ CN 26886-OCF₂H 3,4-Cl₂ CN 2689 6-OCF₂H 3,5-Cl₂ CN 2690 6-OCF₂H 2-F, 3-Cl CN2691 6-OCF₂H 2-F, 4-Cl CN 2692 6-OCF₂H 2-F, 5-Cl CN 2693 6-OCF₂H 2-F,6-Cl CN 2694 6-OCF₂H 2,6-F₂, 4-Cl CN 2695 6-OCF₂H 3-F, 4-Cl CN 26966-OCF₂H 3-Cl, 5-F CN 2697 6-OCF₂H 2-Cl, 5-F CN 2698 6-OCF₂H 3-CN, 4-ClCN 2699 6-OCF₂H 3-NO₂, 4-Cl CN 2700 6-OCF₂H 2-F, 4-Br CN 2701 H 4-F NO₂2702 H 4-Cl NO₂ 2703 H 4-Br NO₂ 2704 H H NO₂ 2705 H 4-Me NO₂ 2706 H 4-CNNO₂ 2707 H 4-NO₂ NO₂ 2708 H 4-OMe NO₂ 2709 H 3-F NO₂ 2710 H 3-Cl NO₂2711 H 3-Br NO₂ 2712 H 3-Me NO₂ 2713 H 3-CN NO₂ 2714 H 3-NO₂ NO₂ 2715 H3-OMe NO₂ 2716 H 2-F NO₂ 2717 H 2-Cl NO₂ 2718 H 2-Br NO₂ 2719 H 2-Me NO₂2720 H 2-CN NO₂ 2721 H 2-NO₂ NO₂ 2722 H 2-OMe NO₂ 2723 H 2,3-F₂ NO₂ 2724H 2,4-F₂ NO₂ 2725 H 2,5-F₂ NO₂ 2726 H 2,6-F₂ NO₂ 2727 H 3,4-F₂ NO₂ 2728H 3,5-F₂ NO₂ 2729 H 2,3-Cl₂ NO₂ 2730 H 2,4-Cl₂ NO₂ 2731 H 2,5-Cl₂ NO₂2732 H 2,6-Cl₂ NO₂ 2733 H 3,4-Cl₂ NO₂ 2734 H 3,5-Cl₂ NO₂ 2735 H 2-F,3-Cl NO₂ 2736 H 2-F, 4-Cl NO₂ 2737 H 2-F, 5-Cl NO₂ 2738 H 2-F, 6-Cl NO₂2739 H 2,6-F₂, 4-Cl NO₂ 2740 H 3-F, 4-Cl NO₂ 2741 H 3-Cl, 5-F NO₂ 2742 H2-Cl, 5-F NO₂ 2743 H 3-CN, 4-Cl NO₂ 2744 H 3-NO₂, 4-Cl NO₂ 2745 H 2-F,4-Br NO₂ 2746 6-F 4-F NO₂ 2747 6-F 4-Cl NO₂ 2748 6-F 4-Br NO₂ 2749 6-F HNO₂ 2750 6-F 4-Me NO₂ 2751 6-F 4-CN NO₂ 2752 6-F 4-NO₂ NO₂ 2753 6-F4-OMe NO₂ 2754 6-F 3-F NO₂ 2755 6-F 3-Cl NO₂ 2756 6-F 3-Br NO₂ 2757 6-F3-Me NO₂ 2758 6-F 3-CN NO₂ 2759 6-F 3-NO₂ NO₂ 2760 6-F 3-OMe NO₂ 27616-F 2-F NO₂ 2762 6-F 2-Cl NO₂ 2763 6-F 2-Br NO₂ 2764 6-F 2-Me NO₂ 27656-F 2-CN NO₂ 2766 6-F 2-NO₂ NO₂ 2767 6-F 2-OMe NO₂ 2768 6-F 2,3-F₂ NO₂2769 6-F 2,4-F₂ NO₂ 2770 6-F 2,5-F₂ NO₂ 2771 6-F 2,6-F₂ NO₂ 2772 6-F3,4-F₂ NO₂ 2773 6-F 3,5-F₂ NO₂ 2774 6-F 2,3-Cl₂ NO₂ 2775 6-F 2,4-Cl₂ NO₂2776 6-F 2,5-Cl₂ NO₂ 2777 6-F 2,6-Cl₂ NO₂ 2778 6-F 3,4-Cl₂ NO₂ 2779 6-F3,5-Cl₂ NO₂ 2780 6-F 2-F, 3-Cl NO₂ 2781 6-F 2-F, 4-Cl NO₂ 2782 6-F 2-F,5-Cl NO₂ 2783 6-F 2-F, 6-Cl NO₂ 2784 6-F 2,6-F₂, 4-Cl NO₂ 2785 6-F 3-F,4-Cl NO₂ 2786 6-F 3-Cl, 5-F NO₂ 2787 6-F 2-Cl, 5-F NO₂ 2788 6-F 3-CN,4-Cl NO₂ 2789 6-F 3-NO₂, 4-Cl NO₂ 2790 6-F 2-F, 4-Br NO₂ 2791 6-Cl 4-FNO₂ 2792 6-Cl 4-Cl NO₂ 2793 6-Cl 4-Br NO₂ 2794 6-Cl H NO₂ 2795 6-Cl 4-MeNO₂ 2796 6-Cl 4-CN NO₂ 2797 6-Cl 4-NO₂ NO₂ 2798 6-Cl 4-OMe NO₂ 2799 6-Cl3-F NO₂ 2800 6-Cl 3-Cl NO₂ 2801 6-Cl 3-Br NO₂ 2802 6-Cl 3-Me NO₂ 28036-Cl 3-CN NO₂ 2804 6-Cl 3-NO₂ NO₂ 2805 6-Cl 3-OMe NO₂ 2806 6-Cl 2-F NO₂2807 6-Cl 2-Cl NO₂ 2808 6-Cl 2-Br NO₂ 2809 6-Cl 2-Me NO₂ 2810 6-Cl 2-CNNO₂ 2811 6-Cl 2-NO₂ NO₂ 2812 6-Cl 2-OMe NO₂ 2813 6-Cl 2,3-F₂ NO₂ 28146-Cl 2,4-F₂ NO₂ 2815 6-Cl 2,5-F₂ NO₂ 2816 6-Cl 2,6-F₂ NO₂ 2817 6-Cl3,4-F₂ NO₂ 2818 6-Cl 3,5-F₂ NO₂ 2819 6-Cl 2,3-Cl₂ NO₂ 2820 6-Cl 2,4-Cl₂NO₂ 2821 6-Cl 2,5-Cl₂ NO₂ 2822 6-Cl 2,6-Cl₂ NO₂ 2823 6-Cl 3,4-Cl₂ NO₂2824 6-Cl 3,5-Cl₂ NO₂ 2825 6-Cl 2-F, 3-Cl NO₂ 2826 6-Cl 2-F, 4-Cl NO₂2827 6-Cl 2-F, 5-Cl NO₂ 2828 6-Cl 2-F, 6-Cl NO₂ 2829 6-Cl 2,6-F₂, 4-ClNO₂ 2830 6-Cl 3-F, 4-Cl NO₂ 2831 6-Cl 3-Cl, 5-F NO₂ 2832 6-Cl 2-Cl, 5-FNO₂ 2833 6-Cl 3-CN, 4-Cl NO₂ 2834 6-Cl 3-NO₂, 4-Cl NO₂ 2835 6-Cl 2-F,4-Br NO₂ 2836 6-Br 4-F NO₂ 2837 6-Br 4-Cl NO₂ 2838 6-Br 4-Br NO₂ 28396-Br H NO₂ 2840 6-Br 4-Me NO₂ 2841 6-Br 4-CN NO₂ 2842 6-Br 4-NO₂ NO₂2843 6-Br 4-OMe NO₂ 2844 6-Br 3-F NO₂ 2845 6-Br 3-Cl NO₂ 2846 6-Br 3-BrNO₂ 2847 6-Br 3-Me NO₂ 2848 6-Br 3-CN NO₂ 2849 6-Br 3-NO₂ NO₂ 2850 6-Br3-OMe NO₂ 2851 6-Br 2-F NO₂ 2852 6-Br 2-Cl NO₂ 2853 6-Br 2-Br NO₂ 28546-Br 2-Me NO₂ 2855 6-Br 2-CN NO₂ 2856 6-Br 2-NO₂ NO₂ 2857 6-Br 2-OMe NO₂2858 6-Br 2,3-F₂ NO₂ 2859 6-Br 2,4-F₂ NO₂ 2860 6-Br 2,5-F₂ NO₂ 2861 6-Br2,6-F₂ NO₂ 2862 6-Br 3,4-F₂ NO₂ 2863 6-Br 3,5-F₂ NO₂ 2864 6-Br 2,3-Cl₂NO₂ 2865 6-Br 2,4-Cl₂ NO₂ 2866 6-Br 2,5-Cl₂ NO₂ 2867 6-Br 2,6-Cl₂ NO₂2868 6-Br 3,4-Cl₂ NO₂ 2869 6-Br 3,5-Cl₂ NO₂ 2870 6-Br 2-F, 3-Cl NO₂ 28716-Br 2-F, 4-Cl NO₂ 2872 6-Br 2-F, 5-Cl NO₂ 2873 6-Br 2-F, 6-Cl NO₂ 28746-Br 2,6-F₂, 4-Cl NO₂ 2875 6-Br 3-F, 4-Cl NO₂ 2876 6-Br 3-Cl, 5-F NO₂2877 6-Br 2-Cl, 5-F NO₂ 2878 6-Br 3-CN, 4-Cl NO₂ 2879 6-Br 3-NO₂, 4-ClNO₂ 2880 6-Br 2-F, 4-Br NO₂ 2881 6-CN 4-F NO₂ 2882 6-CN 4-Cl NO₂ 28836-CN 4-Br NO₂ 2884 6-CN H NO₂ 2885 6-CN 4-Me NO₂ 2886 6-CN 4-CN NO₂ 28876-CN 4-NO₂ NO₂ 2888 6-CN 4-OMe NO₂ 2889 6-CN 3-F NO₂ 2890 6-CN 3-Cl NO₂2891 6-CN 3-Br NO₂ 2892 6-CN 3-Me NO₂ 2893 6-CN 3-CN NO₂ 2894 6-CN 3-NO₂NO₂ 2895 6-CN 3-OMe NO₂ 2896 6-CN 2-F NO₂ 2897 6-CN 2-Cl NO₂ 2898 6-CN2-Br NO₂ 2899 6-CN 2-Me NO₂ 2900 6-CN 2-CN NO₂ 2901 6-CN 2-NO₂ NO₂ 29026-CN 2-OMe NO₂ 2903 6-CN 2,3-F₂ NO₂ 2904 6-CN 2,4-F₂ NO₂ 2905 6-CN2,5-F₂ NO₂ 2906 6-CN 2,6-F₂ NO₂ 2907 6-CN 3,4-F₂ NO₂ 2908 6-CN 3,5-F₂NO₂ 2909 6-CN 2,3-Cl₂ NO₂ 2910 6-CN 2,4-Cl₂ NO₂ 2911 6-CN 2,5-Cl₂ NO₂2912 6-CN 2,6-Cl₂ NO₂ 2913 6-CN 3,4-Cl₂ NO₂ 2914 6-CN 3,5-Cl₂ NO₂ 29156-CN 2-F, 3-Cl NO₂ 2916 6-CN 2-F, 4-Cl NO₂ 2917 6-CN 2-F, 5-Cl NO₂ 29186-CN 2-F, 6-Cl NO₂ 2919 6-CN 2,6-F₂, 4-Cl NO₂ 2920 6-CN 3-F, 4-Cl NO₂2921 6-CN 3-Cl, 5-F NO₂ 2922 6-CN 2-Cl, 5-F NO₂ 2923 6-CN 3-CN, 4-Cl NO₂2924 6-CN 3-NO₂, 4-Cl NO₂ 2925 6-CN 2-F, 4-Br NO₂ 2926 6-Me 4-F NO₂ 29276-Me 4-Cl NO₂ 2928 6-Me 4-Br NO₂ 2929 6-Me H NO₂ 2930 6-Me 4-Me NO₂ 29316-Me 4-CN NO₂ 2932 6-Me 4-NO₂ NO₂ 2933 6-Me 4-OMe NO₂ 2934 6-Me 3-F NO₂2935 6-Me 3-Cl NO₂ 2936 6-Me 3-Br NO₂ 2937 6-Me 3-Me NO₂ 2938 6-Me 3-CNNO₂ 2939 6-Me 3-NO₂ NO₂ 2940 6-Me 3-OMe NO₂ 2941 6-Me 2-F NO₂ 2942 6-Me2-Cl NO₂ 2943 6-Me 2-Br NO₂ 2944 6-Me 2-Me NO₂ 2945 6-Me 2-CN NO₂ 29466-Me 2-NO₂ NO₂ 2947 6-Me 2-OMe NO₂ 2948 6-Me 2,3-F₂ NO₂ 2949 6-Me 2,4-F₂NO₂ 2950 6-Me 2,5-F₂ NO₂ 2951 6-Me 2,6-F₂ NO₂ 2952 6-Me 3,4-F₂ NO₂ 29536-Me 3,5-F₂ NO₂ 2954 6-Me 2,3-Cl₂ NO₂ 2955 6-Me 2,4-Cl₂ NO₂ 2956 6-Me2,5-Cl₂ NO₂ 2957 6-Me 2,6-Cl₂ NO₂ 2958 6-Me 3,4-Cl₂ NO₂ 2959 6-Me3,5-Cl₂ NO₂ 2960 6-Me 2-F, 3-Cl NO₂ 2961 6-Me 2-F, 4-Cl NO₂ 2962 6-Me2-F, 5-Cl NO₂ 2963 6-Me 2-F, 6-Cl NO₂ 2964 6-Me 2,6-F₂, 4-Cl NO₂ 29656-Me 3-F, 4-Cl NO₂ 2966 6-Me 3-Cl, 5-F NO₂ 2967 6-Me 2-Cl, 5-F NO₂ 29686-Me 3-CN, 4-Cl NO₂ 2969 6-Me 3-NO₂, 4-Cl NO₂ 2970 6-Me 2-F, 4-Br NO₂2971 6-OMe 4-F NO₂ 2972 6-OMe 4-Cl NO₂ 2973 6-OMe 4-Br NO₂ 2974 6-OMe HNO₂ 2975 6-OMe 4-Me NO₂ 2976 6-OMe 4-CN NO₂ 2977 6-OMe 4-NO₂ NO₂ 29786-OMe 4-OMe NO₂ 2979 6-OMe 3-F NO₂ 2980 6-OMe 3-Cl NO₂ 2981 6-OMe 3-BrNO₂ 2982 6-OMe 3-Me NO₂ 2983 6-OMe 3-CN NO₂ 2984 6-OMe 3-NO₂ NO₂ 29856-OMe 3-OMe NO₂ 2986 6-OMe 2-F NO₂ 2987 6-OMe 2-Cl NO₂ 2988 6-OMe 2-BrNO₂ 2989 6-OMe 2-Me NO₂ 2990 6-OMe 2-CN NO₂ 2991 6-OMe 2-NO₂ NO₂ 29926-OMe 2-OMe NO₂ 2993 6-OMe 2,3-F₂ NO₂ 2994 6-OMe 2,4-F₂ NO₂ 2995 6-OMe2,5-F₂ NO₂ 2996 6-OMe 2,6-F₂ NO₂ 2997 6-OMe 3,4-F₂ NO₂ 2998 6-OMe 3,5-F₂NO₂ 2999 6-OMe 2,3-Cl₂ NO₂ 3000 6-OMe 2,4-Cl₂ NO₂ 3001 6-OMe 2,5-Cl₂ NO₂3002 6-OMe 2,6-Cl₂ NO₂ 3003 6-OMe 3,4-Cl₂ NO₂ 3004 6-OMe 3,5-Cl₂ NO₂3005 6-OMe 2-F, 3-Cl NO₂ 3006 6-OMe 2-F, 4-Cl NO₂ 3007 6-OMe 2-F, 5-ClNO₂ 3008 6-OMe 2-F, 6-Cl NO₂ 3009 6-OMe 2,6-F₂, 4-Cl NO₂ 3010 6-OMe 3-F,4-Cl NO₂ 3011 6-OMe 3-Cl, 5-F NO₂ 3012 6-OMe 2-Cl, 5-F NO₂ 3013 6-OMe3-CN, 4-Cl NO₂ 3014 6-OMe 3-NO₂, 4-Cl NO₂ 3015 6-OMe 2-F, 4-Br NO₂ 30162-F 4-F NO₂ 3017 2-F 4-Cl NO₂ 3018 2-F 4-Br NO₂ 3019 2-F H NO₂ 3020 2-F4-Me NO₂ 3021 2-F 4-CN NO₂ 3022 2-F 4-NO₂ NO₂ 3023 2-F 4-OMe NO₂ 30242-F 3-F NO₂ 3025 2-F 3-Cl NO₂ 3026 2-F 3-Br NO₂ 3027 2-F 3-Me NO₂ 30282-F 3-CN NO₂ 3029 2-F 3-NO₂ NO₂ 3030 2-F 3-OMe NO₂ 3031 2-F 2-F NO₂ 30322-F 2-Cl NO₂ 3033 2-F 2-Br NO₂ 3034 2-F 2-Me NO₂ 3035 2-F 2-CN NO₂ 30362-F 2-NO₂ NO₂ 3037 2-F 2-OMe NO₂ 3038 2-F 2,3-F₂ NO₂ 3039 2-F 2,4-F₂ NO₂3040 2-F 2,5-F₂ NO₂ 3041 2-F 2,6-F₂ NO₂ 3042 2-F 3,4-F₂ NO₂ 3043 2-F3,5-F₂ NO₂ 3044 2-F 2,3-Cl₂ NO₂ 3045 2-F 2,4-Cl₂ NO₂ 3046 2-F 2,5-Cl₂NO₂ 3047 2-F 2,6-Cl₂ NO₂ 3048 2-F 3,4-Cl₂ NO₂ 3049 2-F 3,5-Cl₂ NO₂ 30502-F 2-F, 3-Cl NO₂ 3051 2-F 2-F, 4-Cl NO₂ 3052 2-F 2-F, 5-Cl NO₂ 3053 2-F2-F, 6-Cl NO₂ 3054 2-F 2,6-F₂, 4-Cl NO₂ 3055 2-F 3-F, 4-Cl NO₂ 3056 2-F3-Cl, 5-F NO₂ 3057 2-F 2-Cl, 5-F NO₂ 3058 2-F 3-CN, 4-Cl NO₂ 3059 2-F3-NO₂, 4-Cl NO₂ 3060 2-F 2-F, 4-Br NO₂ 3061 4-F 4-F NO₂ 3062 4-F 4-ClNO₂ 3063 4-F 4-Br NO₂ 3064 4-F H NO₂ 3065 4-F 4-Me NO₂ 3066 4-F 4-CN NO₂3067 4-F 4-NO₂ NO₂ 3068 4-F 4-OMe NO₂ 3069 4-F 3-F NO₂ 3070 4-F 3-Cl NO₂3071 4-F 3-Br NO₂ 3072 4-F 3-Me NO₂ 3073 4-F 3-CN NO₂ 3074 4-F 3-NO₂ NO₂3075 4-F 3-OMe NO₂ 3076 4-F 2-F NO₂ 3077 4-F 2-Cl NO₂ 3078 4-F 2-Br NO₂3079 4-F 2-Me NO₂ 3080 4-F 2-CN NO₂ 3081 4-F 2-NO₂ NO₂ 3082 4-F 2-OMeNO₂ 3083 4-F 2,3-F₂ NO₂ 3084 4-F 2,4-F₂ NO₂ 3085 4-F 2,5-F₂ NO₂ 3086 4-F2,6-F₂ NO₂ 3087 4-F 3,4-F₂ NO₂ 3088 4-F 3,5-F₂ NO₂ 3089 4-F 2,3-Cl₂ NO₂3090 4-F 2,4-Cl₂ NO₂ 3091 4-F 2,5-Cl₂ NO₂ 3092 4-F 2,6-Cl₂ NO₂ 3093 4-F3,4-Cl₂ NO₂ 3094 4-F 3,5-Cl₂ NO₂ 3095 4-F 2-F, 3-Cl NO₂ 3096 4-F 2-F,4-Cl NO₂ 3097 4-F 2-F, 5-Cl NO₂ 3098 4-F 2-F, 6-Cl NO₂ 3099 4-F 2,6-F₂,4-Cl NO₂ 3100 4-F 3-F, 4-Cl NO₂ 3101 4-F 3-Cl, 5-F NO₂ 3102 4-F 2-Cl,5-F NO₂ 3103 4-F 3-CN, 4-Cl NO₂ 3104 4-F 3-NO₂, 4-Cl NO₂ 3105 4-F 2-F,4-Br NO₂ 3106 2-Cl 4-F NO₂ 3107 2-Cl 4-Cl NO₂ 3108 2-Cl 4-Br NO₂ 31092-Cl H NO₂ 3110 2-Cl 4-Me NO₂ 3111 2-Cl 4-CN NO₂ 3112 2-Cl 4-NO₂ NO₂3113 2-Cl 4-OMe NO₂ 3114 2-Cl 3-F NO₂ 3115 2-Cl 3-Cl NO₂ 3116 2-Cl 3-BrNO₂ 3117 2-Cl 3-Me NO₂ 3118 2-Cl 3-CN NO₂ 3119 2-Cl 3-NO₂ NO₂ 3120 2-Cl3-OMe NO₂ 3121 2-Cl 2-F NO₂ 3122 2-Cl 2-Cl NO₂ 3123 2-Cl 2-Br NO₂ 31242-Cl 2-Me NO₂ 3125 2-Cl 2-CN NO₂ 3126 2-Cl 2-NO₂ NO₂ 3127 2-Cl 2-OMe NO₂3128 2-Cl 2,3-F₂ NO₂ 3129 2-Cl 2,4-F₂ NO₂ 3130 2-Cl 2,5-F₂ NO₂ 3131 2-Cl2,6-F₂ NO₂ 3132 2-Cl 3,4-F₂ NO₂ 3133 2-Cl 3,5-F₂ NO₂ 3134 2-Cl 2,3-Cl₂NO₂ 3135 2-Cl 2,4-Cl₂ NO₂ 3136 2-Cl 2,5-Cl₂ NO₂ 3137 2-Cl 2,6-Cl₂ NO₂3138 2-Cl 3,4-Cl₂ NO₂ 3139 2-Cl 3,5-Cl₂ NO₂ 3140 2-Cl 2-F, 3-Cl NO₂ 31412-Cl 2-F, 4-Cl NO₂ 3142 2-Cl 2-F, 5-Cl NO₂ 3143 2-Cl 2-F, 6-Cl NO₂ 31442-Cl 2,6-F₂, 4-Cl NO₂ 3145 2-Cl 3-F, 4-Cl NO₂ 3146 2-Cl 3-Cl, 5-F NO₂3147 2-Cl 2-Cl, 5-F NO₂ 3148 2-Cl 3-CN, 4-Cl NO₂ 3149 2-Cl 3-NO₂, 4-ClNO₂ 3150 2-Cl 2-F, 4-Br NO₂ 3151 4-Cl 4-F NO₂ 3152 4-Cl 4-Cl NO₂ 31534-Cl 4-Br NO₂ 3154 4-Cl H NO₂ 3155 4-Cl 4-Me NO₂ 3156 4-Cl 4-CN NO₂ 31574-Cl 4-NO₂ NO₂ 3158 4-Cl 4-OMe NO₂ 3159 4-Cl 3-F NO₂ 3160 4-Cl 3-Cl NO₂3161 4-Cl 3-Br NO₂ 3162 4-Cl 3-Me NO₂ 3163 4-Cl 3-CN NO₂ 3164 4-Cl 3-NO₂NO₂ 3165 4-Cl 3-OMe NO₂ 3166 4-Cl 2-F NO₂ 3167 4-Cl 2-Cl NO₂ 3168 4-Cl2-Br NO₂ 3169 4-Cl 2-Me NO₂ 3170 4-Cl 2-CN NO₂ 3171 4-Cl 2-NO₂ NO₂ 31724-Cl 2-OMe NO₂ 3173 4-Cl 2,3-F₂ NO₂ 3174 4-Cl 2,4-F₂ NO₂ 3175 4-Cl2,5-F₂ NO₂ 3176 4-Cl 2,6-F₂ NO₂ 3177 4-Cl 3,4-F₂ NO₂ 3178 4-Cl 3,5-F₂NO₂ 3179 4-Cl 2,3-Cl₂ NO₂ 3180 4-Cl 2,4-Cl₂ NO₂ 3181 4-Cl 2,5-Cl₂ NO₂3182 4-Cl 2,6-Cl₂ NO₂ 3183 4-Cl 3,4-Cl₂ NO₂ 3184 4-Cl 3,5-Cl₂ NO₂ 31854-Cl 2-F, 3-Cl NO₂ 3186 4-Cl 2-F, 4-Cl NO₂ 3187 4-Cl 2-F, 5-Cl NO₂ 31884-Cl 2-F, 6-Cl NO₂ 3189 4-Cl 2,6-F₂, 4-Cl NO₂ 3190 4-Cl 3-F, 4-Cl NO₂3191 4-Cl 3-Cl, 5-F NO₂ 3192 4-Cl 2-Cl, 5-F NO₂ 3193 4-Cl 3-CN, 4-Cl NO₂3194 4-Cl 3-NO₂, 4-Cl NO₂ 3195 4-Cl 2-F, 4-Br NO₂ 3196 6-OCF₂H 4-F NO₂3197 6-OCF₂H 4-Cl NO₂ 3198 6-OCF₂H 4-Br NO₂ 3199 6-OCF₂H H NO₂ 32006-OCF₂H 4-Me NO₂ 3201 6-OCF₂H 4-CN NO₂ 3202 6-OCF₂H 4-NO₂ NO₂ 32036-OCF₂H 4-OMe NO₂ 3204 6-OCF₂H 3-F NO₂ 3205 6-OCF₂H 3-Cl NO₂ 32066-OCF₂H 3-Br NO₂ 3207 6-OCF₂H 3-Me NO₂ 3208 6-OCF₂H 3-CN NO₂ 32096-OCF₂H 3-NO₂ NO₂ 3210 6-OCF₂H 3-OMe NO₂ 3211 6-OCF₂H 2-F NO₂ 32126-OCF₂H 2-Cl NO₂ 3213 6-OCF₂H 2-Br NO₂ 3214 6-OCF₂H 2-Me NO₂ 32156-OCF₂H 2-CN NO₂ 3216 6-OCF₂H 2-NO₂ NO₂ 3217 6-OCF₂H 2-OMe NO₂ 32186-OCF₂H 2,3-F₂ NO₂ 3219 6-OCF₂H 2,4-F₂ NO₂ 3220 6-OCF₂H 2,5-F₂ NO₂ 32216-OCF₂H 2,6-F₂ NO₂ 3222 6-OCF₂H 3,4-F₂ NO₂ 3223 6-OCF₂H 3,5-F₂ NO₂ 32246-OCF₂H 2,3-Cl₂ NO₂ 3225 6-OCF₂H 2,4-Cl₂ NO₂ 3226 6-OCF₂H 2,5-Cl₂ NO₂3227 6-OCF₂H 2,6-Cl₂ NO₂ 3228 6-OCF₂H 3,4-Cl₂ NO₂ 3229 6-OCF₂H 3,5-Cl₂NO₂ 3230 6-OCF₂H 2-F, 3-Cl NO₂ 3231 6-OCF₂H 2-F, 4-Cl NO₂ 3232 6-OCF₂H2-F, 5-Cl NO₂ 3233 6-OCF₂H 2-F, 6-Cl NO₂ 3234 6-OCF₂H 2,6-F₂, 4-Cl NO₂3235 6-OCF₂H 3-F, 4-Cl NO₂ 3236 6-OCF₂H 3-Cl, 5-F NO₂ 3237 6-OCF₂H 2-Cl,5-F NO₂ 3238 6-OCF₂H 3-CN, 4-Cl NO₂ 3239 6-OCF₂H 3-NO₂, 4-Cl NO₂ 32406-OCF₂H 2-F, 4-Br NO₂ 3241 H 4-F CO₂Me 3242 H 4-Cl CO₂Me 3243 H 4-BrCO₂Me 3244 H H CO₂Me 3245 H 4-Me CO₂Me 3246 H 4-CN CO₂Me 3247 H 4-NO₂CO₂Me 3248 H 4-OMe CO₂Me 3249 H 3-F CO₂Me 3250 H 3-Cl CO₂Me 3251 H 3-BrCO₂Me 3252 H 3-Me CO₂Me 3253 H 3-CN CO₂Me 3254 H 3-NO₂ CO₂Me 3255 H3-OMe CO₂Me 3256 H 2-F CO₂Me 3257 H 2-Cl CO₂Me 3258 H 2-Br CO₂Me 3259 H2-Me CO₂Me 3260 H 2-CN CO₂Me 3261 H 2-NO₂ CO₂Me 3262 H 2-OMe CO₂Me 3263H 2,3-F₂ CO₂Me 3264 H 2,4-F₂ CO₂Me 3265 H 2,5-F₂ CO₂Me 3266 H 2,6-F₂CO₂Me 3267 H 3,4-F₂ CO₂Me 3268 H 3,5-F₂ CO₂Me 3269 H 2,3-Cl₂ CO₂Me 3270H 2,4-Cl₂ CO₂Me 3271 H 2,5-Cl₂ CO₂Me 3272 H 2,6-Cl₂ CO₂Me 3273 H 3,4-Cl₂CO₂Me 3274 H 3,5-Cl₂ CO₂Me 3275 H 2-F, 3-Cl CO₂Me 3276 H 2-F, 4-Cl CO₂Me3277 H 2-F, 5-Cl CO₂Me 3278 H 2-F, 6-Cl CO₂Me 3279 H 2,6-F₂, 4-Cl CO₂Me3280 H 3-F, 4-Cl CO₂Me 3281 H 3-Cl, 5-F CO₂Me 3282 H 2-Cl, 5-F CO₂Me3283 H 3-CN, 4-Cl CO₂Me 3284 H 3-NO₂, 4-Cl CO₂Me 3285 H 2-F, 4-Br CO₂Me3286 6-F 4-F CO₂Me 3287 6-F 4-Cl CO₂Me 3288 6-F 4-Br CO₂Me 3289 6-F HCO₂Me 3290 6-F 4-Me CO₂Me 3291 6-F 4-CN CO₂Me 3292 6-F 4-NO₂ CO₂Me 32936-F 4-OMe CO₂Me 3294 6-F 3-F CO₂Me 3295 6-F 3-Cl CO₂Me 3296 6-F 3-BrCO₂Me 3297 6-F 3-Me CO₂Me 3298 6-F 3-CN CO₂Me 3299 6-F 3-NO₂ CO₂Me 33006-F 3-OMe CO₂Me 3301 6-F 2-F CO₂Me 3302 6-F 2-Cl CO₂Me 3303 6-F 2-BrCO₂Me 3304 6-F 2-Me CO₂Me 3305 6-F 2-CN CO₂Me 3306 6-F 2-NO₂ CO₂Me 33076-F 2-OMe CO₂Me 3308 6-F 2,3-F₂ CO₂Me 3309 6-F 2,4-F₂ CO₂Me 3310 6-F2,5-F₂ CO₂Me 3311 6-F 2,6-F₂ CO₂Me 3312 6-F 3,4-F₂ CO₂Me 3313 6-F 3,5-F₂CO₂Me 3314 6-F 2,3-Cl₂ CO₂Me 3315 6-F 2,4-Cl₂ CO₂Me 3316 6-F 2,5-Cl₂CO₂Me 3317 6-F 2,6-Cl₂ CO₂Me 3318 6-F 3,4-Cl₂ CO₂Me 3319 6-F 3,5-Cl₂CO₂Me 3320 6-F 2-F, 3-Cl CO₂Me 3321 6-F 2-F, 4-Cl CO₂Me 3322 6-F 2-F,5-Cl CO₂Me 3323 6-F 2-F, 6-Cl CO₂Me 3324 6-F 2,6-F₂, 4-Cl CO₂Me 3325 6-F3-F, 4-Cl CO₂Me 3326 6-F 3-Cl, 5-F CO₂Me 3327 6-F 2-Cl, 5-F CO₂Me 33286-F 3-CN, 4-Cl CO₂Me 3329 6-F 3-NO₂, 4-Cl CO₂Me 3330 6-F 2-F, 4-Br CO₂Me3331 6-Cl 4-F CO₂Me 3332 6-Cl 4-Cl CO₂Me 3333 6-Cl 4-Br CO₂Me 3334 6-ClH CO₂Me 3335 6-Cl 4-Me CO₂Me 3336 6-Cl 4-CN CO₂Me 3337 6-Cl 4-NO₂ CO₂Me3338 6-Cl 4-OMe CO₂Me 3339 6-Cl 3-F CO₂Me 3340 6-Cl 3-Cl CO₂Me 3341 6-Cl3-Br CO₂Me 3342 6-Cl 3-Me CO₂Me 3343 6-Cl 3-CN CO₂Me 3344 6-Cl 3-NO₂CO₂Me 3345 6-Cl 3-OMe CO₂Me 3346 6-Cl 2-F CO₂Me 3347 6-Cl 2-Cl CO₂Me3348 6-Cl 2-Br CO₂Me 3349 6-Cl 2-Me CO₂Me 3350 6-Cl 2-CN CO₂Me 3351 6-Cl2-NO₂ CO₂Me 3352 6-Cl 2-OMe CO₂Me 3353 6-Cl 2,3-F₂ CO₂Me 3354 6-Cl2,4-F₂ CO₂Me 3355 6-Cl 2,5-F₂ CO₂Me 3356 6-Cl 2,6-F₂ CO₂Me 3357 6-Cl3,4-F₂ CO₂Me 3358 6-Cl 3,5-F₂ CO₂Me 3359 6-Cl 2,3-Cl₂ CO₂Me 3360 6-Cl2,4-Cl₂ CO₂Me 3361 6-Cl 2,5-Cl₂ CO₂Me 3362 6-Cl 2,6-Cl₂ CO₂Me 3363 6-Cl3,4-Cl₂ CO₂Me 3364 6-Cl 3,5-Cl₂ CO₂Me 3365 6-Cl 2-F, 3-Cl CO₂Me 33666-Cl 2-F, 4-Cl CO₂Me 3367 6-Cl 2-F, 5-Cl CO₂Me 3368 6-Cl 2-F, 6-Cl CO₂Me3369 6-Cl 2,6-F₂, 4-Cl CO₂Me 3370 6-Cl 3-F, 4-Cl CO₂Me 3371 6-Cl 3-Cl,5-F CO₂Me 3372 6-Cl 2-Cl, 5-F CO₂Me 3373 6-Cl 3-CN, 4-Cl CO₂Me 3374 6-Cl3-NO₂, 4-Cl CO₂Me 3375 6-Cl 2-F, 4-Br CO₂Me 3376 6-Br 4-F CO₂Me 33776-Br 4-Cl CO₂Me 3378 6-Br 4-Br CO₂Me 3379 6-Br H CO₂Me 3380 6-Br 4-MeCO₂Me 3381 6-Br 4-CN CO₂Me 3382 6-Br 4-NO₂ CO₂Me 3383 6-Br 4-OMe CO₂Me3384 6-Br 3-F CO₂Me 3385 6-Br 3-Cl CO₂Me 3386 6-Br 3-Br CO₂Me 3387 6-Br3-Me CO₂Me 3388 6-Br 3-CN CO₂Me 3389 6-Br 3-NO₂ CO₂Me 3390 6-Br 3-OMeCO₂Me 3391 6-Br 2-F CO₂Me 3392 6-Br 2-Cl CO₂Me 3393 6-Br 2-Br CO₂Me 33946-Br 2-Me CO₂Me 3395 6-Br 2-CN CO₂Me 3396 6-Br 2-NO₂ CO₂Me 3397 6-Br2-OMe CO₂Me 3398 6-Br 2,3-F₂ CO₂Me 3399 6-Br 2,4-F₂ CO₂Me 3400 6-Br2,5-F₂ CO₂Me 3401 6-Br 2,6-F₂ CO₂Me 3402 6-Br 3,4-F₂ CO₂Me 3403 6-Br3,5-F₂ CO₂Me 3404 6-Br 2,3-Cl₂ CO₂Me 3405 6-Br 2,4-Cl₂ CO₂Me 3406 6-Br2,5-Cl₂ CO₂Me 3407 6-Br 2,6-Cl₂ CO₂Me 3408 6-Br 3,4-Cl₂ CO₂Me 3409 6-Br3,5-Cl₂ CO₂Me 3410 6-Br 2-F, 3-Cl CO₂Me 3411 6-Br 2-F, 4-Cl CO₂Me 34126-Br 2-F, 5-Cl CO₂Me 3413 6-Br 2-F, 6-Cl CO₂Me 3414 6-Br 2,6-F₂, 4-ClCO₂Me 3415 6-Br 3-F, 4-Cl CO₂Me 3416 6-Br 3-Cl, 5-F CO₂Me 3417 6-Br2-Cl, 5-F CO₂Me 3418 6-Br 3-CN, 4-Cl CO₂Me 3419 6-Br 3-NO₂, 4-Cl CO₂Me3420 6-Br 2-F, 4-Br CO₂Me 3421 6-CN 4-F CO₂Me 3422 6-CN 4-Cl CO₂Me 34236-CN 4-Br CO₂Me 3424 6-CN H CO₂Me 3425 6-CN 4-Me CO₂Me 3426 6-CN 4-CNCO₂Me 3427 6-CN 4-NO₂ CO₂Me 3428 6-CN 4-OMe CO₂Me 3429 6-CN 3-F CO₂Me3430 6-CN 3-Cl CO₂Me 3431 6-CN 3-Br CO₂Me 3432 6-CN 3-Me CO₂Me 3433 6-CN3-CN CO₂Me 3434 6-CN 3-NO₂ CO₂Me 3435 6-CN 3-OMe CO₂Me 3436 6-CN 2-FCO₂Me 3437 6-CN 2-Cl CO₂Me 3438 6-CN 2-Br CO₂Me 3439 6-CN 2-Me CO₂Me3440 6-CN 2-CN CO₂Me 3441 6-CN 2-NO₂ CO₂Me 3442 6-CN 2-OMe CO₂Me 34436-CN 2,3-F₂ CO₂Me 3444 6-CN 2,4-F₂ CO₂Me 3445 6-CN 2,5-F₂ CO₂Me 34466-CN 2,6-F₂ CO₂Me 3447 6-CN 3,4-F₂ CO₂Me 3448 6-CN 3,5-F₂ CO₂Me 34496-CN 2,3-Cl₂ CO₂Me 3450 6-CN 2,4-Cl₂ CO₂Me 3451 6-CN 2,5-Cl₂ CO₂Me 34526-CN 2,6-Cl₂ CO₂Me 3453 6-CN 3,4-Cl₂ CO₂Me 3454 6-CN 3,5-Cl₂ CO₂Me 34556-CN 2-F, 3-Cl CO₂Me 3456 6-CN 2-F, 4-Cl CO₂Me 3457 6-CN 2-F, 5-Cl CO₂Me3458 6-CN 2-F, 6-Cl CO₂Me 3459 6-CN 2,6-F₂, 4-Cl CO₂Me 3460 6-CN 3-F,4-Cl CO₂Me 3461 6-CN 3-Cl, 5-F CO₂Me 3462 6-CN 2-Cl, 5-F CO₂Me 3463 6-CN3-CN, 4-Cl CO₂Me 3464 6-CN 3-NO₂, 4-Cl CO₂Me 3465 6-CN 2-F, 4-Br CO₂Me3466 6-Me 4-F CO₂Me 3467 6-Me 4-Cl CO₂Me 3468 6-Me 4-Br CO₂Me 3469 6-MeH CO₂Me 3470 6-Me 4-Me CO₂Me 3471 6-Me 4-CN CO₂Me 3472 6-Me 4-NO₂ CO₂Me3473 6-Me 4-OMe CO₂Me 3474 6-Me 3-F CO₂Me 3475 6-Me 3-Cl CO₂Me 3476 6-Me3-Br CO₂Me 3477 6-Me 3-Me CO₂Me 3478 6-Me 3-CN CO₂Me 3479 6-Me 3-NO₂CO₂Me 3480 6-Me 3-OMe CO₂Me 3481 6-Me 2-F CO₂Me 3482 6-Me 2-Cl CO₂Me3483 6-Me 2-Br CO₂Me 3484 6-Me 2-Me CO₂Me 3485 6-Me 2-CN CO₂Me 3486 6-Me2-NO₂ CO₂Me 3487 6-Me 2-OMe CO₂Me 3488 6-Me 2,3-F₂ CO₂Me 3489 6-Me2,4-F₂ CO₂Me 3490 6-Me 2,5-F₂ CO₂Me 3491 6-Me 2,6-F₂ CO₂Me 3492 6-Me3,4-F₂ CO₂Me 3493 6-Me 3,5-F₂ CO₂Me 3494 6-Me 2,3-Cl₂ CO₂Me 3495 6-Me2,4-Cl₂ CO₂Me 3496 6-Me 2,5-Cl₂ CO₂Me 3497 6-Me 2,6-Cl₂ CO₂Me 3498 6-Me3,4-Cl₂ CO₂Me 3499 6-Me 3,5-Cl₂ CO₂Me 3500 6-Me 2-F, 3-Cl CO₂Me 35016-Me 2-F, 4-Cl CO₂Me 3502 6-Me 2-F, 5-Cl CO₂Me 3503 6-Me 2-F, 6-Cl CO₂Me3504 6-Me 2,6-F₂, 4-Cl CO₂Me 3505 6-Me 3-F, 4-Cl CO₂Me 3506 6-Me 3-Cl,5-F CO₂Me 3507 6-Me 2-Cl, 5-F CO₂Me 3508 6-Me 3-CN, 4-Cl CO₂Me 3509 6-Me3-NO₂, 4-Cl CO₂Me 3510 6-Me 2-F, 4-Br CO₂Me 3511 6-OMe 4-F CO₂Me 35126-OMe 4-Cl CO₂Me 3513 6-OMe 4-Br CO₂Me 3514 6-OMe H CO₂Me 3515 6-OMe4-Me CO₂Me 3516 6-OMe 4-CN CO₂Me 3517 6-OMe 4-NO₂ CO₂Me 3518 6-OMe 4-OMeCO₂Me 3519 6-OMe 3-F CO₂Me 3520 6-OMe 3-Cl CO₂Me 3521 6-OMe 3-Br CO₂Me3522 6-OMe 3-Me CO₂Me 3523 6-OMe 3-CN CO₂Me 3524 6-OMe 3-NO₂ CO₂Me 35256-OMe 3-OMe CO₂Me 3526 6-OMe 2-F CO₂Me 3527 6-OMe 2-Cl CO₂Me 3528 6-OMe2-Br CO₂Me 3529 6-OMe 2-Me CO₂Me 3530 6-OMe 2-CN CO₂Me 3531 6-OMe 2-NO₂CO₂Me 3532 6-OMe 2-OMe CO₂Me 3533 6-OMe 2,3-F₂ CO₂Me 3534 6-OMe 2,4-F₂CO₂Me 3535 6-OMe 2,5-F₂ CO₂Me 3536 6-OMe 2,6-F₂ CO₂Me 3537 6-OMe 3,4-F₂CO₂Me 3538 6-OMe 3,5-F₂ CO₂Me 3539 6-OMe 2,3-Cl₂ CO₂Me 3540 6-OMe2,4-Cl₂ CO₂Me 3541 6-OMe 2,5-Cl₂ CO₂Me 3542 6-OMe 2,6-Cl₂ CO₂Me 35436-OMe 3,4-Cl₂ CO₂Me 3544 6-OMe 3,5-Cl₂ CO₂Me 3545 6-OMe 2-F, 3-Cl CO₂Me3546 6-OMe 2-F, 4-Cl CO₂Me 3547 6-OMe 2-F, 5-Cl CO₂Me 3548 6-OMe 2-F,6-Cl CO₂Me 3549 6-OMe 2,6-F₂, 4-Cl CO₂Me 3550 6-OMe 3-F, 4-Cl CO₂Me 35516-OMe 3-Cl, 5-F CO₂Me 3552 6-OMe 2-Cl, 5-F CO₂Me 3553 6-OMe 3-CN, 4-ClCO₂Me 3554 6-OMe 3-NO₂, 4-Cl CO₂Me 3555 6-OMe 2-F, 4-Br CO₂Me 3556 2-F4-F CO₂Me 3557 2-F 4-Cl CO₂Me 3558 2-F 4-Br CO₂Me 3559 2-F H CO₂Me 35602-F 4-Me CO₂Me 3561 2-F 4-CN CO₂Me 3562 2-F 4-NO₂ CO₂Me 3563 2-F 4-OMeCO₂Me 3564 2-F 3-F CO₂Me 3565 2-F 3-Cl CO₂Me 3566 2-F 3-Br CO₂Me 35672-F 3-Me CO₂Me 3568 2-F 3-CN CO₂Me 3569 2-F 3-NO₂ CO₂Me 3570 2-F 3-OMeCO₂Me 3571 2-F 2-F CO₂Me 3572 2-F 2-Cl CO₂Me 3573 2-F 2-Br CO₂Me 35742-F 2-Me CO₂Me 3575 2-F 2-CN CO₂Me 3576 2-F 2-NO₂ CO₂Me 3577 2-F 2-OMeCO₂Me 3578 2-F 2,3-F₂ CO₂Me 3579 2-F 2,4-F₂ CO₂Me 3580 2-F 2,5-F₂ CO₂Me3581 2-F 2,6-F₂ CO₂Me 3582 2-F 3,4-F₂ CO₂Me 3583 2-F 3,5-F₂ CO₂Me 35842-F 2,3-Cl₂ CO₂Me 3585 2-F 2,4-Cl₂ CO₂Me 3586 2-F 2,5-Cl₂ CO₂Me 3587 2-F2,6-Cl₂ CO₂Me 3588 2-F 3,4-Cl₂ CO₂Me 3589 2-F 3,5-Cl₂ CO₂Me 3590 2-F2-F, 3-Cl CO₂Me 3591 2-F 2-F, 4-Cl CO₂Me 3592 2-F 2-F, 5-Cl CO₂Me 35932-F 2-F, 6-Cl CO₂Me 3594 2-F 2,6-F₂, 4-Cl CO₂Me 3595 2-F 3-F, 4-Cl CO₂Me3596 2-F 3-Cl, 5-F CO₂Me 3597 2-F 2-Cl, 5-F CO₂Me 3598 2-F 3-CN, 4-ClCO₂Me 3599 2-F 3-NO₂, 4-Cl CO₂Me 3600 2-F 2-F, 4-Br CO₂Me 3601 4-F 4-FCO₂Me 3602 4-F 4-Cl CO₂Me 3603 4-F 4-Br CO₂Me 3604 4-F H CO₂Me 3605 4-F4-Me CO₂Me 3606 4-F 4-CN CO₂Me 3607 4-F 4-NO₂ CO₂Me 3608 4-F 4-OMe CO₂Me3609 4-F 3-F CO₂Me 3610 4-F 3-Cl CO₂Me 3611 4-F 3-Br CO₂Me 3612 4-F 3-MeCO₂Me 3613 4-F 3-CN CO₂Me 3614 4-F 3-NO₂ CO₂Me 3615 4-F 3-OMe CO₂Me 36164-F 2-F CO₂Me 3617 4-F 2-Cl CO₂Me 3618 4-F 2-Br CO₂Me 3619 4-F 2-MeCO₂Me 3620 4-F 2-CN CO₂Me 3621 4-F 2-NO₂ CO₂Me 3622 4-F 2-OMe CO₂Me 36234-F 2,3-F₂ CO₂Me 3624 4-F 2,4-F₂ CO₂Me 3625 4-F 2,5-F₂ CO₂Me 3626 4-F2,6-F₂ CO₂Me 3627 4-F 3,4-F₂ CO₂Me 3628 4-F 3,5-F₂ CO₂Me 3629 4-F2,3-Cl₂ CO₂Me 3630 4-F 2,4-Cl₂ CO₂Me 3631 4-F 2,5-Cl₂ CO₂Me 3632 4-F2,6-Cl₂ CO₂Me 3633 4-F 3,4-Cl₂ CO₂Me 3634 4-F 3,5-Cl₂ CO₂Me 3635 4-F2-F, 3-Cl CO₂Me 3636 4-F 2-F, 4-Cl CO₂Me 3637 4-F 2-F, 5-Cl CO₂Me 36384-F 2-F, 6-Cl CO₂Me 3639 4-F 2,6-F₂, 4-Cl CO₂Me 3640 4-F 3-F, 4-Cl CO₂Me3641 4-F 3-Cl, 5-F CO₂Me 3642 4-F 2-Cl, 5-F CO₂Me 3643 4-F 3-CN, 4-ClCO₂Me 3644 4-F 3-NO₂, 4-Cl CO₂Me 3645 4-F 2-F, 4-Br CO₂Me 3646 2-Cl 4-FCO₂Me 3647 2-Cl 4-Cl CO₂Me 3648 2-Cl 4-Br CO₂Me 3649 2-Cl H CO₂Me 36502-Cl 4-Me CO₂Me 3651 2-Cl 4-CN CO₂Me 3652 2-Cl 4-NO₂ CO₂Me 3653 2-Cl4-OMe CO₂Me 3654 2-Cl 3-F CO₂Me 3655 2-Cl 3-Cl CO₂Me 3656 2-Cl 3-BrCO₂Me 3657 2-Cl 3-Me CO₂Me 3658 2-Cl 3-CN CO₂Me 3659 2-Cl 3-NO₂ CO₂Me3660 2-Cl 3-OMe CO₂Me 3661 2-Cl 2-F CO₂Me 3662 2-Cl 2-Cl CO₂Me 3663 2-Cl2-Br CO₂Me 3664 2-Cl 2-Me CO₂Me 3665 2-Cl 2-CN CO₂Me 3666 2-Cl 2-NO₂CO₂Me 3667 2-Cl 2-OMe CO₂Me 3668 2-Cl 2,3-F₂ CO₂Me 3669 2-Cl 2,4-F₂CO₂Me 3670 2-Cl 2,5-F₂ CO₂Me 3671 2-Cl 2,6-F₂ CO₂Me 3672 2-Cl 3,4-F₂CO₂Me 3673 2-Cl 3,5-F₂ CO₂Me 3674 2-Cl 2,3-Cl₂ CO₂Me 3675 2-Cl 2,4-Cl₂CO₂Me 3676 2-Cl 2,5-Cl₂ CO₂Me 3677 2-Cl 2,6-Cl₂ CO₂Me 3678 2-Cl 3,4-Cl₂CO₂Me 3679 2-Cl 3,5-Cl₂ CO₂Me 3680 2-Cl 2-F, 3-Cl CO₂Me 3681 2-Cl 2-F,4-Cl CO₂Me 3682 2-Cl 2-F, 5-Cl CO₂Me 3683 2-Cl 2-F, 6-Cl CO₂Me 3684 2-Cl2,6-F₂, 4-Cl CO₂Me 3685 2-Cl 3-F, 4-Cl CO₂Me 3686 2-Cl 3-Cl, 5-F CO₂Me3687 2-Cl 2-Cl, 5-F CO₂Me 3688 2-Cl 3-CN, 4-Cl CO₂Me 3689 2-Cl 3-NO₂,4-Cl CO₂Me 3690 2-Cl 2-F, 4-Br CO₂Me 3691 4-Cl 4-F CO₂Me 3692 4-Cl 4-ClCO₂Me 3693 4-Cl 4-Br CO₂Me 3694 4-Cl H CO₂Me 3695 4-Cl 4-Me CO₂Me 36964-Cl 4-CN CO₂Me 3697 4-Cl 4-NO₂ CO₂Me 3698 4-Cl 4-OMe CO₂Me 3699 4-Cl3-F CO₂Me 3700 4-Cl 3-Cl CO₂Me 3701 4-Cl 3-Br CO₂Me 3702 4-Cl 3-Me CO₂Me3703 4-Cl 3-CN CO₂Me 3704 4-Cl 3-NO₂ CO₂Me 3705 4-Cl 3-OMe CO₂Me 37064-Cl 2-F CO₂Me 3707 4-Cl 2-Cl CO₂Me 3708 4-Cl 2-Br CO₂Me 3709 4-Cl 2-MeCO₂Me 3710 4-Cl 2-CN CO₂Me 3711 4-Cl 2-NO₂ CO₂Me 3712 4-Cl 2-OMe CO₂Me3713 4-Cl 2,3-F₂ CO₂Me 3714 4-Cl 2,4-F₂ CO₂Me 3715 4-Cl 2,5-F₂ CO₂Me3716 4-Cl 2,6-F₂ CO₂Me 3717 4-Cl 3,4-F₂ CO₂Me 3718 4-Cl 3,5-F₂ CO₂Me3719 4-Cl 2,3-Cl₂ CO₂Me 3720 4-Cl 2,4-Cl₂ CO₂Me 3721 4-Cl 2,5-Cl₂ CO₂Me3722 4-Cl 2,6-Cl₂ CO₂Me 3723 4-Cl 3,4-Cl₂ CO₂Me 3724 4-Cl 3,5-Cl₂ CO₂Me3725 4-Cl 2-F, 3-Cl CO₂Me 3726 4-Cl 2-F, 4-Cl CO₂Me 3727 4-Cl 2-F, 5-ClCO₂Me 3728 4-Cl 2-F, 6-Cl CO₂Me 3729 4-Cl 2,6-F₂, 4-Cl CO₂Me 3730 4-Cl3-F, 4-Cl CO₂Me 3731 4-Cl 3-Cl, 5-F CO₂Me 3732 4-Cl 2-Cl, 5-F CO₂Me 37334-Cl 3-CN, 4-Cl CO₂Me 3734 4-Cl 3-NO₂, 4-Cl CO₂Me 3735 4-Cl 2-F, 4-BrCO₂Me 3736 6-OCF₂H 4-F CO₂Me 3737 6-OCF₂H 4-Cl CO₂Me 3738 6-OCF₂H 4-BrCO₂Me 3739 6-OCF₂H H CO₂Me 3740 6-OCF₂H 4-Me CO₂Me 3741 6-OCF₂H 4-CNCO₂Me 3742 6-OCF₂H 4-NO₂ CO₂Me 3743 6-OCF₂H 4-OMe CO₂Me 3744 6-OCF₂H 3-FCO₂Me 3745 6-OCF₂H 3-Cl CO₂Me 3746 6-OCF₂H 3-Br CO₂Me 3747 6-OCF₂H 3-MeCO₂Me 3748 6-OCF₂H 3-CN CO₂Me 3749 6-OCF₂H 3-NO₂ CO₂Me 3750 6-OCF₂H3-OMe CO₂Me 3751 6-OCF₂H 2-F CO₂Me 3752 6-OCF₂H 2-Cl CO₂Me 3753 6-OCF₂H2-Br CO₂Me 3754 6-OCF₂H 2-Me CO₂Me 3755 6-OCF₂H 2-CN CO₂Me 3756 6-OCF₂H2-NO₂ CO₂Me 3757 6-OCF₂H 2-OMe CO₂Me 3758 6-OCF₂H 2,3-F₂ CO₂Me 37596-OCF₂H 2,4-F₂ CO₂Me 3760 6-OCF₂H 2,5-F₂ CO₂Me 3761 6-OCF₂H 2,6-F₂ CO₂Me3762 6-OCF₂H 3,4-F₂ CO₂Me 3763 6-OCF₂H 3,5-F₂ CO₂Me 3764 6-OCF₂H 2,3-Cl₂CO₂Me 3765 6-OCF₂H 2,4-Cl₂ CO₂Me 3766 6-OCF₂H 2,5-Cl₂ CO₂Me 3767 6-OCF₂H2,6-Cl₂ CO₂Me 3768 6-OCF₂H 3,4-Cl₂ CO₂Me 3769 6-OCF₂H 3,5-Cl₂ CO₂Me 37706-OCF₂H 2-F, 3-Cl CO₂Me 3771 6-OCF₂H 2-F, 4-Cl CO₂Me 3772 6-OCF₂H 2-F,5-Cl CO₂Me 3773 6-OCF₂H 2-F, 6-Cl CO₂Me 3774 6-OCF₂H 2,6-F₂, 4-Cl CO₂Me3775 6-OCF₂H 3-F, 4-Cl CO₂Me 3776 6-OCF₂H 3-Cl, 5-F CO₂Me 3777 6-OCF₂H2-Cl, 5-F CO₂Me 3778 6-OCF₂H 3-CN, 4-Cl CO₂Me 3779 6-OCF₂H 3-NO₂, 4-ClCO₂Me 3780 6-OCF₂H 2-F, 4-Br CO₂Me 3781 H 3-F, 4-OMe F 3782 H 3-F, 4-OMeCl 3783 H 3-F, 4-OMe Br 3784 H 3-F, 4-OMe Me 3785 H 3-F, 4-OMe CN 3786 H3-F, 4-OMe NO₂ 3787 H 3-F, 4-OMe CO₂Me 3788 6-F 3-F, 4-OMe F 3789 6-F3-F, 4-OMe Cl 3790 6-F 3-F, 4-OMe Br 3791 6-F 3-F, 4-OMe Me 3792 6-F3-F, 4-OMe CN 3793 6-F 3-F, 4-OMe NO₂ 3794 6-F 3-F, 4-OMe CO₂Me 3795 H3-F, 4-CN F 3796 H 3-F, 4-CN Cl 3797 H 3-F, 4-CN Br 3798 H 3-F, 4-CN Me3799 H 3-F, 4-CN CN 3800 H 3-F, 4-CN NO₂ 3801 H 3-F, 4-CN CO₂Me 3802 6-F3-F, 4-CN F 3803 6-F 3-F, 4-CN Cl 3804 6-F 3-F, 4-CN Br 3805 6-F 3-F,4-CN Me 3806 6-F 3-F, 4-CN CN 3807 6-F 3-F, 4-CN NO₂ 3808 6-F 3-F, 4-CNCO₂Me 3809 6-Cl 3-F, 4-CN F 3810 6-Cl 3-F, 4-CN Cl 3811 6-Cl 3-F, 4-CNBr 3812 6-Cl 3-F, 4-CN Me 3813 6-Cl 3-F, 4-CN CN 3814 6-Cl 3-F, 4-CN NO₂3815 6-Cl 3-F, 4-CN CO₂Me 3816 6-CN 3-F, 4-CN F 3817 6-CN 3-F, 4-CN Cl3818 6-CN 3-F, 4-CN Br 3819 6-CN 3-F, 4-CN Me 3820 6-CN 3-F, 4-CN CN3821 6-CN 3-F, 4-CN NO₂ 3822 6-CN 3-F, 4-CN CO₂Me 3823 H 3-F, 4-NO₂ F3824 H 3-F, 4-NO₂ Cl 3825 H 3-F, 4-NO₂ Br 3826 H 3-F, 4-NO₂ Me 3827 H3-F, 4-NO₂ CN 3828 H 3-F, 4-NO₂ NO₂ 3829 H 3-F, 4-NO₂ CO₂Me 3830 6-F3-F, 4-NO₂ F 3831 6-F 3-F, 4-NO₂ Cl 3832 6-F 3-F, 4-NO₂ Br 3833 6-F 3-F,4-NO₂ Me 3834 6-F 3-F, 4-NO₂ CN 3835 6-F 3-F, 4-NO₂ NO₂ 3836 6-F 3-F,4-NO₂ CO₂Me 3837 6-Cl 3-F, 4-NO₂ F 3838 6-Cl 3-F, 4-NO₂ Cl 3839 6-Cl3-F, 4-NO₂ Br 3840 6-Cl 3-F, 4-NO₂ Me 3841 6-Cl 3-F, 4-NO₂ CN 3842 6-Cl3-F, 4-NO₂ NO₂ 3843 6-Cl 3-F, 4-NO₂ CO₂Me 3844 6-CN 3-F, 4-NO₂ F 38456-CN 3-F, 4-NO₂ Cl 3846 6-CN 3-F, 4-NO₂ Br 3847 6-CN 3-F, 4-NO₂ Me 38486-CN 3-F, 4-NO₂ CN 3849 6-CN 3-F, 4-NO₂ NO₂ 3850 6-CN 3-F, 4-NO₂ CO₂Me3851 H 3-Cl, 4-F F 3852 H 3-Cl, 4-F Cl 3853 H 3-Cl, 4-F Br 3854 H 3-Cl,4-F Me 3855 H 3-Cl, 4-F CN 3856 H 3-Cl, 4-F NO₂ 3857 H 3-Cl, 4-F CO₂Me3858 6-F 3-Cl, 4-F F 3859 6-F 3-Cl, 4-F Cl 3860 6-F 3-Cl, 4-F Br 38616-F 3-Cl, 4-F Me 3862 6-F 3-Cl, 4-F CN 3863 6-F 3-Cl, 4-F NO₂ 3864 6-F3-Cl, 4-F CO₂Me 3865 6-Cl 3-Cl, 4-F F 3866 6-Cl 3-Cl, 4-F Cl 3867 6-Cl3-Cl, 4-F Br 3868 6-Cl 3-Cl, 4-F Me 3869 6-Cl 3-Cl, 4-F CN 3870 6-Cl3-Cl, 4-F NO₂ 3871 6-Cl 3-Cl, 4-F CO₂Me 3872 6-CN 3-Cl, 4-F F 3873 6-CN3-Cl, 4-F Cl 3874 6-CN 3-Cl, 4-F Br 3875 6-CN 3-Cl, 4-F Me 3876 6-CN3-Cl, 4-F CN 3877 6-CN 3-Cl, 4-F NO₂ 3878 6-CN 3-Cl, 4-F CO₂Me 3879 H3-F, 4-Br F 3880 H 3-F, 4-Br Cl 3881 H 3-F, 4-Br Br 3882 H 3-F, 4-Br Me3883 H 3-F, 4-Br CN 3884 H 3-F, 4-Br NO₂ 3885 H 3-F, 4-Br CO₂Me 3886 6-F3-F, 4-Br F 3887 6-F 3-F, 4-Br Cl 3888 6-F 3-F, 4-Br Br 3889 6-F 3-F,4-Br Me 3890 6-F 3-F, 4-Br CN 3891 6-F 3-F, 4-Br NO₂ 3892 6-F 3-F, 4-BrCO₂Me 3893 6-Cl 3-F, 4-Br F 3894 6-Cl 3-F, 4-Br Cl 3895 6-Cl 3-F, 4-BrBr 3896 6-Cl 3-F, 4-Br Me 3897 6-Cl 3-F, 4-Br CN 3898 6-Cl 3-F, 4-Br NO₂3899 6-Cl 3-F, 4-Br CO₂Me 3900 6-CN 3-F, 4-Br F 3901 6-CN 3-F, 4-Br Cl3902 6-CN 3-F, 4-Br Br 3903 6-CN 3-F, 4-Br Me 3904 6-CN 3-F, 4-Br CN3905 6-CN 3-F, 4-Br NO₂ 3906 6-CN 3-F, 4-Br CO₂Me 3907 H 3-CN, 4-F F3908 H 3-CN, 4-F Cl 3909 H 3-CN, 4-F Br 3910 H 3-CN, 4-F Me 3911 H 3-CN,4-F CN 3912 H 3-CN, 4-F NO₂ 3913 H 3-CN, 4-F CO₂Me 3914 6-F 3-CN, 4-F F3915 6-F 3-CN, 4-F Cl 3916 6-F 3-CN, 4-F Br 3917 6-F 3-CN, 4-F Me 39186-F 3-CN, 4-F CN 3919 6-F 3-CN, 4-F NO₂ 3920 6-F 3-CN, 4-F CO₂Me 39216-Cl 3-CN, 4-F F 3922 6-Cl 3-CN, 4-F Cl 3923 6-Cl 3-CN, 4-F Br 3924 6-Cl3-CN, 4-F Me 3925 6-Cl 3-CN, 4-F CN 3926 6-Cl 3-CN, 4-F NO₂ 3927 6-Cl3-CN, 4-F CO₂Me 3928 6-CN 3-CN, 4-F F 3929 6-CN 3-CN, 4-F Cl 3930 6-CN3-CN, 4-F Br 3931 6-CN 3-CN, 4-F Me 3932 6-CN 3-CN, 4-F CN 3933 6-CN3-CN, 4-F NO₂ 3934 6-CN 3-CN, 4-F CO₂Me 3935 H 4-CF₃ F 3936 H 4-CF₃ Cl3937 H 4-CF₃ Br 3938 H 4-CF₃ Me 3939 H 4-CF₃ CN 3940 H 4-CF₃ NO₂ 3941 H4-CF₃ CO₂Me 3942 6-F 4-CF₃ F 3943 6-F 4-CF₃ Cl 3944 6-F 4-CF₃ Br 39456-F 4-CF₃ Me 3946 6-F 4-CF₃ CN 3947 6-F 4-CF₃ NO₂ 3948 6-F 4-CF₃ CO₂Me3949 6-Cl 4-CF₃ F 3950 6-Cl 4-CF₃ Cl 3951 6-Cl 4-CF₃ Br 3952 6-Cl 4-CF₃Me 3953 6-Cl 4-CF₃ CN 3954 6-Cl 4-CF₃ NO₂ 3955 6-Cl 4-CF₃ CO₂Me 39566-CN 4-CF₃ F 3957 6-CN 4-CF₃ Cl 3958 6-CN 4-CF₃ Br 3959 6-CN 4-CF₃ Me3960 6-CN 4-CF₃ CN 3961 6-CN 4-CF₃ NO₂ 3962 6-CN 4-CF₃ CO₂Me 3963 H4-OCF₃ F 3964 H 4-OCF₃ Cl 3965 H 4-OCF₃ Br 3966 H 4-OCF₃ Me 3967 H4-OCF₃ CN 3968 H 4-OCF₃ NO₂ 3969 H 4-OCF₃ CO₂Me 3970 6-F 4-OCF₃ F 39716-F 4-OCF₃ Cl 3972 6-F 4-OCF₃ Br 3973 6-F 4-OCF₃ Me 3974 6-F 4-OCF₃ CN3975 6-F 4-OCF₃ NO₂ 3976 6-F 4-OCF₃ CO₂Me 3977 6-Cl 4-OCF₃ F 3978 6-Cl4-OCF₃ Cl 3979 6-Cl 4-OCF₃ Br 3980 6-Cl 4-OCF₃ Me 3981 6-Cl 4-OCF₃ CN3982 6-Cl 4-OCF₃ NO₂ 3983 6-Cl 4-OCF₃ CO₂Me 3984 6-CN 4-OCF₃ F 3985 6-CN4-OCF₃ Cl 3986 6-CN 4-OCF₃ Br 3987 6-CN 4-OCF₃ Me 3988 6-CN 4-OCF₃ CN3989 6-CN 4-OCF₃ NO₂ 3990 6-CN 4-OCF₃ CO₂Me

Definition of the Examples in Tables 2 to 2f below:

For reference purposes, specific numbers (=Example Numbers) have beenassigned to the individual compounds in Tables 2 to 2f below, where theExample Number in question is composed of the number of the chemicalformula assigned to the respective table and a “row number” (row number)which refers to the same number in the row of the first column ofTable 1. The chemical structure of Example No. “(formula number) (rownumber)” is thus defined unambiguously by the formula above therespective table by formula number and row number of Table 1, forexample:

The example of No. “Iba1” from Table 2 is the compound of the formula(Ib) in which R⁴=H (=hydrogen) [=formula (Iba)] and (R¹)_(m)=H,(R²)_(n)=4-F and R³=F, defined according to row 1 of Table 1.

The example of No. “Ibd1801” from Table 2 is the compound of the formula(Ib) in which R⁴=n-propyl [=formula (Ibd)] and (R¹)_(m)=6-CN,(R²)_(n)=4-F and R³=Me=CH₃, defined according to row 1801 of Table 1.

This applies correspondingly to the assignment of racemic or opticallyactive threo stereoisomers or erythro stereoisomers. For example, forreference purposes, specific numbers (=Example Numbers) have beenassigned to the compounds of Table 2a, where the number “threo-Iba (rownumber)” refers to the racemic mixture of the threo enantiomers havingthe chemical structure of the formulae (threo-1-Iba) and (threo-2-Iba),each of which has the structural combination of groups (R¹)_(m),(R²)_(n) and R³ according to the row number of Table 1.

TABLE 2 Compounds of the formulae (Ib), (Iba), (Ibb), (Ibc), (Ibd),(Ibe), (Ibf), (Ibg) (Ibh), (Ibi), (Ibj), (Ibk), (Ibl), (Ibm), (Ibn),(Ibo), (Ibp), (Ibq), (Ibr) (Ibs), (Ibt), (Ibu), (Ibv), (Ibw), (Ibx),(Iby) and (Ibz) where (R¹)_(m), (R²)_(n) and R³ are each as defined inTable 1

(Ib)

For definitions of subformulae of formula (Ib), see Table U1 below:

TABLE U1 Formula Radical R⁴ in formula (Ib) (Iba) H (hydrogen atom)(Ibb) methyl (Ibc) ethyl (Ibd) n-propyl (Ibe) isopropyl (Ibf)2,2-difluoroethyl (Ibg) 2,2,2-trifluoroethyl (Ibh) 2-methoxyethyl (Ibi)cyclopropylmethyl (Ibj) (1-methylcyclopropyl)methyl (Ibk) allyl (Ibl)prop-2-yn-1-yl (Ibm) ethynyl (Ibn) prop-1-yn-1-yl (Ibo) benzyl (Ibp)4-chlorobenzyl (Ibq) phenyl (Ibr) methoxymethyl (Ibs) difluoromethyl(Ibt) oxetan-3-yl (Ibu) thietan-3-yl (Ibv) 2-(phenylsulphanyl)ethyl(Ibw) 2-(phenylsulphinyl)ethyl (Ibx) 2-(ethylsulphanyl)ethyl (Iby)2-(ethylsulphinyl)ethyl (Ibz) tetrahydrofuran-2-ylmethylErythro/Threo Mixtures of the Formulae (Iba) to (Ibz):

Examples of compounds of the formulae (Iba) to (Ibz) are the compoundsof the respective formulae (Iba) to (Ibz) in the form of a racemicerythro/threo mixture (ratio 70:30 to 30:70), where the structuralcombination of the groups (R¹)_(m), (R²)_(n) and R³ is defined accordingto a row number of Table 1.

The numeration is carried out according to “(formula)(row number)”without any brackets, for example Iba200=compound of the formula (Iba)having the structural combination of row 200 of Table 1.

TABLES 2a, 2b and 2c Threo, threo-1 and threo-2 compounds of thecompounds of the formulae (Ib), (Iba), (Ibb), (Ibc), (Ibd), (Ibe),(Ibf), (Ibg) (Ibh), (Ibi), (Ibj), (Ibk), (Ibl), (Ibm), (Ibn), (Ibo),(Ibp), (Ibq), (Ibr) (Ibs), (Ibt), (Ibu), (Ibv), (Ibw), (Ibx), (Iby) and(Ibz) where (R¹)_(m), (R²)_(n) and R³ are each as defined in Table 1

(threo-1-Ib)

(threo-2-Ib) (threo-Ib) = (threo-1-Ib) + (threo-2-Ib) (50:50) = (rac.)

For definitions of subformulae of formulae (threo-lb), (threo-1-lb) and(threo-2-lb), see Table U2 below:

TABLE U2 Formula Radical R⁴ in formula (threo-Ib) (threo-Iba) H(hydrogen atom) (threo-1-Iba) H (hydrogen atom) (threo-2-Iba) H(hydrogen atom) (threo-Ibb) methyl (threo-1-Ibb) methyl (threo-2-Ibb)methyl (threo-Ibc) ethyl (threo-1-Ibc) ethyl (threo-2-Ibc) ethyl(threo-Ibd) n-propyl (threo-1-Ibd) n-propyl (threo-2-Ibd) n-propyl(threo-Ibe) isopropyl (threo-1-Ibe) isopropyl (threo-2-Ibe) isopropyl(threo-Ibf) 2,2-difluoroethyl (threo-1-Ibf) 2,2-difluoroethyl(threo-2-Ibf) 2,2-difluoroethyl (threo-Ibg) 2,2,2-trifluoroethyl(threo-1-Ibg) 2,2,2-trifluoroethyl (threo-2-Ibg) 2,2,2-trifluoroethyl(threo-Ibh) 2-methoxyethyl (threo-1-Ibh) 2-methoxyethyl (threo-2-Ibh)2-methoxyethyl (threo-Ibi) cyclopropylmethyl (threo-1-Ibi)cyclopropylmethyl (threo-2-Ibi) cyclopropylmethyl (threo-Ibj)(1-methylcyclopropyl)methyl (threo-1-Ibj) (1-methylcyclopropyl)methyl(threo-2-Ibj) (1-methylcyclopropyl)methyl (threo-Ibk) allyl(threo-1-Ibk) allyl (threo-2-Ibk) allyl (threo-Ibl) prop-2-yn-1-yl(threo-1-Ibl) prop-2-yn-1-yl (threo-2-Ibl) prop-2-yn-1-yl (threo-Ibm)ethynyl (threo-1-Ibm) ethynyl (threo-2-Ibm) ethynyl (threo-Ibn)prop-1-yn-1-yl (threo-1-Ibn) prop-1-yn-1-yl (threo-2-Ibn) prop-1-yn-1-yl(threo-Ibo) benzyl (threo-1-Ibo) benzyl (threo-2-Ibo) benzyl (threo-Ibp)4-chlorobenzyl (threo-1-Ibp) 4-chlorobenzyl (threo-2-Ibp) 4-chlorobenzyl(threo-Ibq) phenyl (threo-1-Ibq) phenyl (threo-2-Ibq) phenyl (threo-Ibr)methoxymethyl (threo-1-Ibr) methoxymethyl (threo-2-Ibr) methoxymethyl(threo-Ibs) difluoromethyl (threo-1-Ibs) difluoromethyl (threo-2-Ibs)difluoromethyl (threo-Ibt) oxetan-3-yl (threo-1-Ibt) oxetan-3-yl(threo-2-Ibt) oxetan-3-yl (threo-Ibu) thietan-3-yl (threo-1-Ibu)thietan-3-yl (threo-2-Ibu) thietan-3-yl (threo-Ibv)2-(phenylsulphanyl)ethyl (threo-1-Ibv) 2-(phenylsulphanyl)ethyl(threo-2-Ibv) 2-(phenylsulphanyl)ethyl (threo-Ibw)2-(phenylsulphinyl)ethyl (threo-1-Ibw) 2-(phenylsulphinyl)ethyl(threo-2-Ibw) 2-(phenylsulphinyl)ethyl (threo-Ibx)2-(ethylsulphanyl)ethyl (threo-1-Ibx) 2-(ethylsulphanyl)ethyl(threo-2-Ibx) 2-(ethylsulphanyl)ethyl (threo-Iby)2-(ethylsulphinyl)ethyl (threo-1-Iby) 2-(ethylsulphinyl)ethyl(threo-2-Iby) 2-(ethylsulphinyl)ethyl (threo-Ibz)tetrahydrofuran-2-ylmethyl (threo-1-Ibz) tetrahydrofuran-2-ylmethyl(threo-2-Ibz) tetrahydrofuran-2-ylmethylTable 2a (Threo Racemates), Examples:

Examples of the compounds of the formulae (threo-Iba) to (threo-Ibz)(see Table U2) are the compounds of the formulae in question in the formof the racemic mixture of the threo isomers where the structuralcombination of groups (R¹)_(m), (R²)_(n) and R³ is defined according toa row number of Table 1.

The numeration is carried out according to “(formula)(row number)”without any brackets, for example threo-Iba200=compound of the formula(threo-Iba) having the structural combination of row 200 of Table 1.

Table 2b (Optically Active Threo-2 Enantiomers): Examples:

Examples of the compounds of the formulae (threo-2-Iba) to (threo-2-Ibz)(see Table U2) are the optically active threo-2 compounds of theformulae in question in enriched form [=(3R,4R)-form having more than90% ee] where the structural combination of groups (R¹)_(m), (R²)_(n)and R³ is defined according to a row number of Table 1.

Compounds are numbered “(formula)(row number)”, without any brackets.For example, No. threo-2-Iba1789 refers to the compound of the formula(threo-2-Iba) in which (R¹)_(m)=6-Br, (R²)_(n)=3,5-Cl₂ and R³=Me.

Table 2c (Optically Active Threo-1 Enantiomers): Examples:

Examples of the compounds of the formulae (threo-1-Iba) to (threo-1-Ibz)(see Table U2) are the optically active threo-1 compounds of theformulae in question in enriched form [=(3S,4S)-form having more than90% ee] where the structural combination of groups (R¹)_(m), (R²)_(n)and R³ is defined according to a row number of Table 1.

Compounds are numbered “(formula)(row number)”, without any brackets.For example, No. threo-1-Ibb5 refers to the compound of the formula(threo-1-Ibb) in which (R¹)_(m)=H, (R²)_(n)=4-Me and R³=F.

TABLES 2d, 2e and 2f Erythro, erythro-1 and erythro-2 compounds of thecompounds of the formulae (Ib), (Iba), (Ibb), (Ibc), (Ibd), (Ibe),(Ibf), (Ibg) (Ibh), (Ibi), (Ibj), (Ibk), (Ibl), (Ibm), (Ibn), (Ibo),(Ibp), (Ibq), (Ibr) (Ibs), (Ibt), (Ibu), (Ibv), (Ibw), (Ibx), (Iby) and(Ibz) where (R¹)_(m), (R²)_(n) and R³ are each as defined in Table 1

(erythro-1-Ib)

(erythro-2-Ib) (erythro-Ib) = (erythro-1-Ib) + (erythro-2-Ib) (50:50) =(rac.)

For definitions of subformulae of formulae (erythro-Ib), (erythro-1-Ib)and (erythro-2-Ib), see Table U3 below:

TABLE U3 Formula Radical R⁴ in formula (erythro-Ib) (erythro-Iba) H(hydrogen atom) (erythro-1-Iba) H (hydrogen atom) (erythro-2-Iba) H(hydrogen atom) (erythro-Ibb) methyl (erythro-1-Ibb) methyl(erythro-2-Ibb) methyl (erythro-Ibc) ethyl (erythro-1-Ibc) ethyl(erythro-2-Ibc) ethyl (erythro-Ibd) n-propyl (erythro-1-Ibd) n-propyl(erythro-2-Ibd) n-propyl (erythro-Ibe) isopropyl (erythro-1-Ibe)isopropyl (erythro-2-Ibe) isopropyl (erythro-Ibf) 2,2-difluoroethyl(erythro-1-Ibf) 2,2-difluoroethyl (erythro-2-Ibf) 2,2-difluoroethyl(erythro-Ibg) 2,2,2-trifluoroethyl (erythro-1-Ibg) 2,2,2-trifluoroethyl(erythro-2-Ibg) 2,2,2-trifluoroethyl (erythro-Ibh) 2-methoxyethyl(erythro-1-Ibh) 2-methoxyethyl (erythro-2-Ibh) 2-methoxyethyl(erythro-Ibi) cyclopropylmethyl (erythro-1-Ibi) cyclopropylmethyl(erythro-2-Ibi) cyclopropylmethyl (erythro-Ibj)(1-methylcyclopropyl)methyl (erythro-1-Ibj) (1-methylcyclopropyl)methyl(erythro-2-Ibj) (1-methylcyclopropyl)methyl (erythro-Ibk) allyl(erythro-1-Ibk) allyl (erythro-2-Ibk) allyl (erythro-Ibl) prop-2-yn-1-yl(erythro-1-Ibl) prop-2-yn-1-yl (erythro-2-Ibl) prop-2-yn-1-yl(erythro-Ibm) ethynyl (erythro-1-Ibm) ethynyl (erythro-2-Ibm) ethynyl(erythro-Ibn) prop-1-yn-1-yl (erythro-1-Ibn) prop-1-yn-1-yl(erythro-2-Ibn) prop-1-yn-1-yl (erythro-Ibo) benzyl (erythro-1-Ibo)benzyl (erythro-2-Ibo) benzyl (erythro-Ibp) 4-chlorobenzyl(erythro-1-Ibp) 4-chlorobenzyl (erythro-2-Ibp) 4-chlorobenzyl(erythro-Ibq) phenyl (erythro-1-Ibq) phenyl (erythro-2-Ibq) phenyl(erythro-Ibr) methoxymethyl (erythro-1-Ibr) methoxymethyl(erythro-2-Ibr) methoxymethyl (erythro-Ibs) difluoromethyl(erythro-1-Ibs) difluoromethyl (erythro-2-Ibs) difluoromethyl(erythro-Ibt) oxetan-3-yl (erythro-1-Ibt) oxetan-3-yl (erythro-2-Ibt)oxetan-3-yl (erythro-Ibu) thietan-3-yl (erythro-1-Ibu) thietan-3-yl(erythro-2-Ibu) thietan-3-yl (erythro-Ibv) 2-(phenylsulphanyl)ethyl(erythro-1-Ibv) 2-(phenylsulphanyl)ethyl (erythro-2-Ibv)2-(phenylsulphanyl)ethyl (erythro-Ibw) 2-(phenylsulphinyl)ethyl(erythro-1-Ibw) 2-(phenylsulphinyl)ethyl (erythro-2-Ibw)2-(phenylsulphinyl)ethyl (erythro-Ibx) 2-(ethylsulphanyl)ethyl(erythro-1-Ibx) 2-(ethylsulphanyl)ethyl (erythro-2-Ibx)2-(ethylsulphanyl)ethyl (erythro-Iby) 2-(ethylsulphinyl)ethyl(erythro-1-Iby) 2-(ethylsulphinyl)ethyl (erythro-2-Iby)2-(ethylsulphinyl)ethyl (erythro-Ibz) tetrahydrofuran-2-ylmethyl(erythro-1-Ibz) tetrahydrofuran-2-ylmethyl (erythro-2-Ibz)tetrahydrofuran-2-ylmethylTable 2d (Erythro Racemates), Examples:

Examples of the compounds of the formulae (erythro-Iba) to (erythro-Ibz)(see Table U3) are the compounds of the formulae in question in the formof the racemic mixture of the erythro isomers where the structuralcombination of groups (R¹)_(m), (R²)_(n) and R³ is defined according toa row number of Table 1.

The numeration is carried out according to “(formula)(row number)”without any brackets, for example erythro-Iba200=compound of the formula(erythro-Iba) having the structural combination of row 200 of Table 1.

Table 2e (Optically Active Erythro-2 Enantiomers): Examples:

Examples of the compounds of the formulae (erythro-2-Iba) to(erythro-2-Ibz) (see Table U3) are the optically active erythro-2compounds of the formulae in question in enriched form [=(3R,4S)-formhaving more than 90% ee] where the structural combination of groups(R¹)_(m), (R²)_(n) and R³ is defined according to a row number of Table1.

Compounds are numbered “(formula)(row number)”, without any brackets.For example, No. erythro-2-Iba1789 refers to the compound of the formula(erythro-2-Iba) in which (R¹)_(m)=6-Br, (R²)_(n)=3,5-Cl₂ and R³=Me.

Table 2f (Optically Active Erythro-1 Enantiomers): Examples:

Examples of the compounds of the formulae (erythro-1-Iba) to(erythro-1-Ibz) (see Table U3) are the optically active erythro-1compounds of the formulae in question in enriched form [=(3S,4R)-formhaving more than 90% ee] where the structural combination of groups(R¹)_(m), (R²)_(n) and R³ is defined according to a row number of Table1.

Compounds are numbered “(formula)(row number)”, without any brackets.For example, No. erythro-1-Ibb5 refers to the compound of the formula(erythro-1-Ibb) in which (R¹)_(m)=H, (R²)_(n)=4-Me and R³=F.

Physical Data for Tables 2a-2f:

Test Methods:

-   1) NMR=¹H-NMR data (400 MHz, CDCl₃); characteristic chemical shifts    [in ppm] are indicated for the example in question,-   2) MS=mass spectrum, measured using a quadrupole instrument;    electrospray ionization (+−), mass range 100-1000; molecular peak M    or [M+H]+ or [M−1]+ or [M−2]+ or [M+1]+ indicated for the example in    question,-   3) HPLC=High Performance Liquid Chromatography, column: Zorbax    Eclipse, 50×3.0, C18 1.8 ym, mobile phase: water+0.06% formic    acid/acrylonitrile+0.06% formic acid, gradient: 90:10, after 2 min    5:95; detector: DAD (210-400 nm); retention time (rt) indicated for    the example in question,-   4) chiral HPLC=HPLC on a chiral column, column: Chiralpak IC,    250×4.6 mm, 5 μm DAIC 83325, detector wavelength: 210 nm; column    temperature 25° C.,    -   mobile phase a: (n-heptane:2-propanol), (60:40), Chromasolv,        flow rate: 1.0 ml/min    -   mobile phase b: (n-heptane:2-propanol), (70:30), Chromasolv,        flow rate: 1.0 ml/min    -   mobile phase c: (n-heptane:2-propanol), (80:20), Chromasolv,        flow rate: 1.0 ml/min    -   mobile phase d: (n-heptane:2-propanol), (90:10), Chromasolv,        flow rate: 0.6 ml/min

Ex. erythro-Ibb2, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.53 (m, 1H), 3.71(s, 3H), 4.56 (d, 1H), 6.95 (d, 2H), 7.08 (dt, 1H), 7.25 (d, 2H), 8.24(bs, 1H), 8.43 (d, 1H)

Ex. erythro-1-Ibb2, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.53 (m, 1H),3.71 (s, 3H), 4.56 (d, 1H), 6.95 (d, 2H), 7.08 (dt, 1H), 7.25 (d, 2H),8.24 (bs, 1H), 8.43 (d, 1H)); chiral HPLC: 29.9 min, mobile phase d

Ex. erythro-2-Ibb2, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.53 (m, 1H),3.71 (s, 3H), 4.56 (d, 1H), 6.95 (d, 2H), 7.08 (dt, 1H), 7.25 (d, 2H),8.24 (bs, 1H), 8.43 (d, 1H)); chiral HPLC: 32.9 min, mobile phase d

Ex. threo-Ibb2, NMR: 2.92 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.18 (d,1H), 7.04 (d, 2H), 7.25 (dt, 1H), 7.28 (d, 2H), 8.15 (bs, 1H), 8.44 (d,1H)

Ex. threo-1-Ibb2, NMR: 2.92 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.18(d, 1H), 7.04 (d, 2H), 7.25 (dt, 1H), 7.28 (d, 2H), 8.15 (bs, 1H), 8.44(d, 1H)); chiral HPLC: 11.7 min, mobile phase c

Ex. threo-2-Ibb2, NMR: 2.92 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.18(d, 1H), 7.04 (d, 2H), 7.25 (dt, 1H), 7.28 (d, 2H), 8.15 (bs, 1H), 8.44(d, 1H)); chiral HPLC: 23.2 min, mobile phase c

Ex. erythro-Ibb4, NMR: 2.89 (dd, 1H), 3.10 (dd, 1H), 3.53 (m, 1H), 3.71(s, 3H), 4.57 (d, 1H), 7.01 (m, 3H), 8.22 (m, 1H), 8.40 (d, 1H)

Ex. threo-Ibb4, NMR: 2.94 (d, 2H), 3.59 (s, 3H), 3.66 (q, 1H), 4.20 (d,1H), 7.07 (m, 2H), 7.20 (m, 1H), 8.14 (m, 1H), 8.40 (d, 1H)

Ex. erythro-Ibb7, NMR: 2.90 (dd, 1H), 3.11 (dd, 1H), 3.69 (m, 1H), 3.71(s, 3H), 4.62 (d, 1H), 7.12 (dt, 1H), 7.23 (d, 2H), 8.15 (d, 2H), 8.27(bs, 1H), 8.46 (d, 1H)

Ex. threo-Ibb7, NMR: 2.98 (d, 2H), 3.60 (s, 3H), 3.80 (q, 1H), 4.25 (d,1H), 7.32 (m, 1H), 7.33 (d, 2H), 8.19 (d, 2H), 8.19 (m, 1H), 8.44 (bs,1H)

Ex. erythro-Ibb9, NMR: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.54 (m, 1H), 3.71(s, 3H), 4.56 (d, 1H), 6.78 (m, 2H), 7.00 (m, 1H), 7.08 (t, 1H), 8.25(m, 1H), 8.43 (d, 1H)

Ex. threo-Ibb9, NMR: 2.93 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.19 (d,1H), 6.83 (m, 1H), 6.88 (d, 1H), 6.98 (m. 1H), 8.17 (t, 1H), 8.43 (d,1H)

Ex. threo-Ibb10, NMR: 2.93 (d, 2H), 3.61 (s, 3H), 3.64 (q, 1H), 4.19 (d,1H), 6.99 (m, 1H), 7.09 (m, 1H), 8.17 (bs, 1H), 8.44 (d, 1H)

Ex. erythro-Ibb25, NMR: 2.81 (dd, 1H), 3.00 (dd, 1H), 3.70 (s, 3H), 3.96(q, 1H), 4.59 (d, 1H), 6.91 (m, 1H), 6.99 (m, 1H), 7.11 (m, 1H), 7.21(dt, 1H), 8.28 (bs, 1H), 8.45 (d, 1H)

Ex. threo-Ibb25, NMR: 3.00 (m, 2H), 3.60 (s, 3H), 3.91 (q, 1H), 4.26 (d,1H), 6.85 (m, 1H), 7.00 (m. 2H), 7.40 (dt, 1H), 8.25 (bs, 1H), 8.44 (d,1H)

Ex. erythro-Ibb26, NMR: 2.88 (d, 2H), 3.59 (s, 3H), 4.11 (q, 1H), 4.46(d, 1H), 6.92 (t, 2H), 7.44 (dt, 1H), 8.39 (bs, 1H), 8.49 (d, 1H)

Ex. erythro-1-Ibb26, NMR: 2.88 (d, 2H), 3.59 (s, 3H), 4.11 (q, 1H), 4.46(d, 1H), 6.92 (t, 2H), 7.44 (dt, 1H), 8.39 (bs, 1H), 8.49 (d, 1H);chiral HPLC: 12.5 min, mobile phase c

Ex. erythro-2-Ibb26, NMR: 2.88 (d, 2H), 3.59 (s, 3H), 4.11 (q, 1H), 4.46(d, 1H), 6.92 (t, 2H), 7.44 (dt, 1H), 8.39 (bs, 1H), 8.49 (d, 1H);chiral HPLC: 13.5 min, mobile phase c

Ex. threo-Ibb26, NMR: 3.15 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17(m, 1H), 4.26 (d, 1H), 6.78 (t, 2H), 7.39 (dt, 1H), 8.10 (bs, 1H), 8.36(bs, 1H)

Ex. threo-1-Ibb26, NMR: 3.15 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17(m, 1H), 4.26 (d, 1H), 6.78 (t, 2H), 7.39 (dt, 1H), 8.10 (bs, 1H), 8.36(bs, 1H); chiral HPLC: 11.7 min, mobile phase c

Ex. threo-2-Ibb26, NMR: 3.15 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17(m, 1H), 4.26 (d, 1H), 6.78 (t, 2H), 7.39 (dt, 1H), 8.10 (bs, 1H), 8.36(bs, 1H); chiral HPLC: 16.5 min, mobile phase c

Ex. erythro-Ibb541, NMR: 2.86 (dd, 1H), 3.06 (dd, 1H), 3.52 (m, 1H),3.71 (s, 3H), 4.50 (d, 1H), 6.98 (d, 2H), 7.32 (t, 1H), 8.24 (d, 1H),8.52 (d, 1H)

Ex. threo-Ibb541, NMR: 2.90 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.14(d, 1H), 7.00 (m, 2H), 7.06 (m, 2H), 7.48 (t, 1H), 8.18 (d, 1H), 8.52(d, 1H)

Ex. erythro-Ibb542, NMR: 2.85 (dd, 1H), 3.05 (dd, 1H), 3.51 (m, 1H),3.70 (s, 3H), 4.50 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.35 (t, 1H),8.25 (d, 1H), 8.52 (d, 1H)

Ex. threo-Ibb542, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.14(d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.50 (t, 1H), 8.19 (d, 1H), 8.53(d, 1H)

Ex. threo-1-Ibb542, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.14(d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.50 (t, 1H), 8.19 (d, 1H), 8.53(d, 1H); chiral HPLC: 11.0 min, mobile phase c

Ex. threo-2-Ibb542, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.14(d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.50 (t, 1H), 8.19 (d, 1H), 8.53(d, 1H); chiral HPLC: 18.5 min, mobile phase c

Ex. erythro-Ibb543, NMR: 2.85 (dd, 1H), 3.05 (dd, 1H), 3.50 (m, 1H),3.70 (s, 3H), 4.50 (d, 1H), 6.89 (d, 2H), 7.36 (s, 1H), 7.42 (d, 2H),8.25 (s, 1H), 8.53 (s, 1H)

Ex. threo-Ibb543, NMR: 2.90 (d, 2H), 3.60 (s, 3H), 3.63 (q, 1H), 4.14(d, 1H), 6.98 (d, 2H), 7.44 (d, 2H), 7.51 (t, 1H), 8.19 (d, 1H), 8.53(d, 1H)

Ex. erythro-Ibb544, NMR: 2.89 (dd, 1H), 3.10 (dd, 1H), 3.52 (m, 1H),3.70 (s, 3H), 4.52 (d, 1H), 7.00 (m, 2H), 7.29 (m, 4H), 8.23 (d, 1H),8.50 (d, 1H)

Ex. threo-Ibb544, NMR: 2.94 (d, 2H), 3.59 (s, 3H), 3.65 (q, 1H), 4.16(d, 1H), 7.07 (m, 2H), 7.29 (m, 3H), 7.45 (t, 1H), 8.16 (d, 1H), 8.60(d, 1H)

Ex. erythro-Ibb546, NMR: 2.87 (dd, 1H), 3.08 (dd, 1H), 3.60 (m, 1H),3.71 (s, 3H), 4.55 (d, 1H), 7.15 (d, 2H), 7.35 (t, 1H), 7.60 (d, 2H),8.27 (d, 1H), 8.55 (d, 1H)

Ex. threo-Ibb546, NMR: 2.94 (d, 2H), 3.60 (s, 3H), 3.73 (q, 1H), 4.18(d, 1H), 7.26 (d, 2H), 7.51 (t, 1H), 7.63 (d, 2H), 8.21 (bs, 1H), 8.55(bs, 1H)

Ex. erythro-Ibb547, NMR: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.68 (m, 1H),3.71 (s, 3H), 4.57 (d, 1H), 7.22 (d, 2H), 7.40 (t, 1H), 8.17 (d, 2H),8.28 (d, 1H), 8.55 (d, 1H)

Ex. threo-Ibb547, NMR: 2.97 (d, 2H), 3.60 (s, 3H), 3.80 (q, 1H), 4.21(d, 1H), 7.34 (d, 2H), 7.55 (t, 1H), 8.20 (d, 2H), 8.23 (bs, 1H), 8.56(bs, 1H)

Ex. erythro-Ibb548, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.47 (m, 1H),3.70 (s, 3H), 3.78 (s, 3H), 4.47 (d, 1H), 6.80 (d, 2H), 6.91 (d, 2H),7.31 (m, 1H), 8.22 (d, 1H), 8.50 (d, 1H)

Ex. threo-Ibb548, NMR: 2.89 (m, 2H), 3.59 (s, 3H), 3.60 (m, 1H), 3.78(s, 3H), 4.12 (d, 1H), 6.81 (d, 2H), 6.98 (d, 2H), 7.46 (t, 1H), 8.15(d, 1H), 8.50 (d, 1H)

Ex. erythro-Ibb553, NMR: 2.87 (dd, 1H), 3.07 (dd, 1H), 3.58 (m, 1H),3.71 (s, 3H), 4.53 (d, 1H), 7.31 (m, 2H), 7.36 (t, 1H), 7.44 (t, 1H),7.62 (m, 1H), 8.27 (d, 1H), 8.55 (d, 1H)

Ex. threo-Ibb553, NMR: 2.93 (d, 2H), 3.61 (s, 3H), 3.71 (q, 1H), 4.17(d, 1H), 7.41 (m, 2H), 7.46 (t, 1H), 7.51 (t, 1H), 7.62 (m, 1H), 8.21(d, 1H), 8.55 (d, 1H)

Ex. erythro-Ibb565, NMR: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.69 (s, 3H),3.94 (q, 1H), 4.54 (d, 1H), 6.93 (m, 1H), 6.99 (m, 1H), 7.10 (m, 1H),7.45 (t, 1H), 8.31 (bs, 1H), 8.54 (d, 1H)

Ex. threo-Ibb565, NMR: 2.99 (m, 2H), 3.60 (s, 3H), 3.91 (q, 1H), 4.22(d, 1H), 6.86 (m, 1H), 6.98 (m. 1H), 7.01 (m, 1H), 7.65 (t, 1H), 8.30(d, 1H), 8.53 (d, 1H)

Ex. erythro-Ibb566, NMR: 2.88 (d, 2H), 3.59 (s, 3H), 4.10 (q, 1H), 4.41(d, 1H), 6.92 (t, 2H), 7.32 (m, 1H), 7.69 (t, 1H), 8.44 (bs, 1H), 8.59(bs, 1H)

Ex. threo-Ibb566, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.18(m, 1H), 4.22 (d, 1H), 6.79 (t, 2H), 7.18 (m, 1H), 7.64 (t, 1H), 8.15(d, 1H), 8.45 (d, 1H)

Ex. threo-1-Ibb566, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H),4.18 (m, 1H), 4.22 (d, 1H), 6.79 (t, 2H), 7.18 (m, 1H), 7.64 (t, 1H),8.15 (d, 1H), 8.45 (d, 1H)); chiral HPLC: 11.5 min, mobile phase c

Ex. threo-2-Ibb566, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H),4.18 (m, 1H), 4.22 (d, 1H), 6.79 (t, 2H), 7.18 (m, 1H), 7.64 (t, 1H),8.15 (d, 1H), 8.45 (d, 1H)); chiral HPLC: 15.4 min, mobile phase c

Ex. Ibb587 (erythro-Ibb587: threo-Ibb587=50:50), NMR:

erythro-Ibb587: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.48 (m, 1H), 3.71 (s,3H), 4.53 (d, 1H), 6.96 (d, 2H), 7.28 (d, 2H), 7.46 (dd, 1H), 7.83 (m,1H)

threo-Ibb587: 2.89 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H),7.03 (d, 2H), 7.30 (d, 2H), 7.61 (dd, 1H), 7.77 (m, 1H)

Ex. erythro-Ibb587: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.48 (m, 1H), 3.71 (s,3H), 4.53 (d, 1H), 6.96 (d, 2H), 7.28 (d, 2H), 7.46 (dd, 1H), 7.83 (m,1H)

Ex. threo-Ibb587: 2.89 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.16 (d,1H), 7.03 (d, 2H), 7.30 (d, 2H), 7.61 (dd, 1H), 7.77 (m, 1H)

Ex. Ibb589 (erythro-Ibb589: threo-Ibb589=50:50), NMR:

erythro-Ibb589: 2.90 (dd, 1H), 3.11 (dd, 1H), 3.48 (m, 1H), 3.71 (s,3H), 4.55 (d, 1H), 7.00 (m, 2H), 7.30 (m, 3H), 7.37 (dd, 1H), 7.81 (m,1H)

threo-Ibb589: 2.94 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.17 (d, 1H),7.05 (m, 2H), 7.54 (dd, 1H), 7.74 (m, 1H)

Ex. erythro-Ibb589: 2.90 (dd, 1H), 3.11 (dd, 1H), 3.48 (m, 1H), 3.71 (s,3H), 4.55 (d, 1H), 7.00 (m, 2H), 7.30 (m, 3H), 7.37 (dd, 1H), 7.81 (m,1H)

Ex. erythro-Ibb592: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.65 (m, 1H), 3.72 (s,3H), 4.59 (d, 1H), 7.25 (d, 2H), 7.53 (dd, 1H), 7.87 (m, 1H), 8.18 (d,2H)

Ex. threo-Ibb592: 2.97 (d, 2H), 3.61 (s, 3H), 3.78 (q, 1H), 4.23 (d,1H), 7.33 (d, 2H), 7.68 (dd, 1H), 7.82 (m, 1H), 8.20 (d, 2H)

Ex. Ibb594 (erythro-Ibb594: threo-Ibb594=54:46), NMR:

erythro-Ibb594: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72 (s,3H), 4.54 (d, 1H), 6.79 (m, 2H), 7.00 (m, 1H), 7.28 (m, 1H), 7.45 (dd,1H), 7.85 (m, 1H)

threo-Ibb594: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.17 (d, 1H),6.83 (m, 2H), 7.01 (m, 1H), 7.28 (m, 1H), 7.61 (dd, 1H), 7.78 (m, 1H)

Ex. erythro-Ibb594: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72 (s,3H), 4.54 (d, 1H), 6.79 (m, 2H), 7.00 (m, 1H), 7.28 (m, 1H), 7.45 (dd,1H), 7.85 (m, 1H)

Ex. Ibb595 (erythro-Ibb595: threo-Ibb595=48:52), NMR:

erythro-Ibb595: 2.85 (dd, 1H), 3.05 (dd, 1H), 3.47 (m, 1H), 3.71 (s,3H), 4.53 (d, 1H), 6.91 (dt, 1H), 7.04 (t, 1H), 7.45 (dd, 1H), 7.86 (m,1H)

threo-Ibb595: 2.91 (m, 2H), 3.61 (q, 1H), 3.62 (s, 3H), 4.18 (d, 1H),6.98 (dt, 1H), 7.10 (t, 1H), 7.62 (dd, 1H), 7.80 (m, 1H)

Ex. erythro-Ibb595: 2.85 (dd, 1H), 3.05 (dd, 1H), 3.47 (m, 1H), 3.71 (s,3H), 4.53 (d, 1H), 6.91 (dt, 1H), 7.04 (t, 1H), 7.24 (t, 1H), 7.30 (m,1H), 7.45 (dd, 1H), 7.86 (m, 1H)

Ex. Ibb610 (erythro-Ibb610: threo-Ibb610=55:45), NMR:

erythro-Ibb610: 2.82 (dd, 1H), 3.01 (dd, 1H), 3.71 (s, 3H), 3.93 (m,1H), 4.58 (d, 1H), 6.94 (m, 1H), 6.99 (m, 1H), 7.12 (m, 1H), 7.59 (dd,1H), 7.90 (m, 1H)

threo-Ibb610: 2.99 (m, 2H), 3.61 (s, 3H), 3.90 (q, 1H), 4.22 (d, 1H),6.86 (m, 1H), 7.00 (m, 2H), 7.79 (m, 1H), 7.88 (m, 2H)

Ex. erythro-Ibb610: 2.82 (dd, 1H), 3.01 (dd, 1H), 3.71 (s, 3H), 3.93 (m,1H), 4.58 (d, 1H), 6.94 (m, 1H), 6.99 (m, 1H), 7.12 (m, 1H), 7.59 (dd,1H), 7.90 (m, 1H)

Ex. Ibb611 (erythro-Ibb611: threo-Ibb611=50:50), NMR:

erythro-Ibb611: 2.88 (dd, 1H), 2.93 (dd, 1H), 3.62 (s, 3H), 4.07 (q,1H), 4.45 (d, 1H), 6.92 (t, 2H), 7.31 (m, 1H), 7.81 (dd, 1H), 8.02 (m,1H)

threo-Ibb611: 3.11 (dd, 1H), 3.24 (dd, 1H), 3.63 (s, 3H), 4.16 (m, 1H),4.22 (d, 1H), 6.81 (t, 2H), 7.23 (m, 1H), 7.74 (m, 1H), 7.78 (dd, 1H)

Ex. erythro-Ibb624: 2.87 (m, 2H), 3.63 (s, 3H), 4.01 (q, 1H), 4.40 (d,1H), 6.98 (d, 2H), 7.84 (dd, 1H), 8.03 (m, 1H)

Ex. threo-Ibb624: 3.07 (dd, 1H), 3.22 (dd, 1H), 3.64 (s, 3H), 4.10 (m,1H), 4.18 (d, 1H), 6.87 (d, 2H), 7.76 (m, 1H), 7.80 (dd, 1H)

Ex. erythro-Ibb1081, NMR: 2.86 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H),3.70 (s, 3H), 4.49 (d, 1H), 6.98 (d, 4H), 7.46 (t, 1H), 8.27 (d, 1H),8.62 (d, 1H)

Ex. threo-Ibb1081, NMR: 2.90 (m, 2H), 3.60 (s, 3H), 3.65 (q, 1H), 4.12(d, 1H), 7.03 (m, 4H), 7.62 (t, 1H), 8.22 (d, 1H), 8.62 (d, 1H)

Ex. Iba1082 (erythro-Iba1082:threo-Iba1082=35:65):

erythro-Iba1082, NMR: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.49 (m, 1H), 4.50(d, 1H), 6.95 (d, 2H), 7.30 (d, 2H), 7.49 (m, 1H)

threo-Iba1082, NMR: 2.93 (m, 2H), 3.64 (q, 1H), 4.14 (d, 1H), 7.05 (d,2H), 7.27 (d, 2H), 7.65 (m, 1H)

Ex. Ibb1082 (erythro-Ibb1082:threo-Ibb1082=58:42):

erythro-Ibb1082, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H), 3.71(s, 3H), 4.49 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.49 (m, 1H)

threo-Ibb1082, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.12 (d,1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.64 (m, 1H)

Ex. erythro-Ibb1082, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H),3.71 (s, 3H), 4.49 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.49 (m, 1H),8.27 (d, 1H), 8.62 (d, 1H)

Ex. erythro-1-Ibb1082, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H),3.71 (s, 3H), 4.49 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.49 (m, 1H),8.27 (d, 1H), 8.62 (d, 1H); chiral HPLC: 28.2 min, mobile phase d

Ex. erythro-2-Ibb1082, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.51 (m, 1H),3.71 (s, 3H), 4.49 (d, 1H), 6.95 (d, 2H), 7.27 (d, 2H), 7.49 (m, 1H),8.27 (d, 1H), 8.62 (d, 1H); chiral HPLC: rt=30.4 min, mobile phase d

Ex. threo-Ibb1082, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.12(d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.64 (m, 1H), 8.22 (d, 1H), 8.63(d, 1H)

Ex. threo-1-Ibb1082, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.12(d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.64 (t, 1H), 8.22 (d, 1H), 8.63(d, 1H); chiral HPLC: rt=6.9 min, mobile phase a

Ex. threo-2-Ibb1082, NMR: 2.89 (d, 2H), 3.60 (s, 3H), 3.64 (q, 1H), 4.12(d, 1H), 7.04 (d, 2H), 7.29 (d, 2H), 7.64 (t, 1H), 8.22 (d, 1H), 8.63(d, 1H); chiral HPLC: rt=9.9 min, mobile phase a

Ex. Ibc1082 (erythro-Ibc1082:threo-Ibc1082=58:42):

erythro-Ibc1082, NMR: 1.24 (t, 3H), 2.83 (dd, 1H), 3.03 (dd, 1H), 3.51(m, 1H), 4.14 (q, 2H), 4.48 (d, 1H), 6.95 (d, 2H), 7.28 (d, 2H), 7.49(m, 1H), 8.27 (m, 1H), 8.63 (m, 1H)

threo-Ibc1082, NMR: 1.16 (t, 3H), 2.89 (d, 2H), 3.63 (q, 1H), 4.03 (m,2H), 4.12 (d, 1H), 7.04 (d, 2H), 7.26 (d, 2H), 7.64 (m, 1H), 8.22 (m,1H), 8.63 (m, 1H)

erythro-Ibc1082, NMR: 1.24 (t, 3H), 2.83 (dd, 1H), 3.03 (dd, 1H), 3.51(m, 1H), 4.14 (q, 2H), 4.48 (d, 1H), 6.95 (d, 2H), 7.28 (d, 2H), 7.49(m, 1H), 8.27 (m, 1H), 8.63 (m, 1H)

threo-Ibc1082, NMR: 1.16 (t, 3H), 2.89 (d, 2H), 3.63 (q, 1H), 4.03 (m,2H), 4.12 (d, 1H), 7.04 (d, 2H), 7.26 (d, 2H), 7.64 (m, 1H), 8.22 (m,1H), 8.63 (m, 1H)

Ex. Ibv1082 (erythro-Ibv1082:threo-Ibv1082=58:42):

erythro-Ibv1082, NMR: 3.09 (t, 2H), 3.47 (m, 1H), 4.28 (t, 2H), 4.47 (d,1H), 6.93 (d, 2H), 7.49 (t, 1H), 8.28 (d, 1H), 8.63 (d, 1H)

threo-Ibv1082, NMR: 3.02 (t, 2H), 3.59 (q, 1H), 4.12 (d, 1H), 4.16 (m,2H), 7.01 (d, 2H), 7.67 (t, 1H), 8.21 (d, 1H), 8.63 (d, 1H)

Ex. erythro-Ibb1083, NMR in [D₆-DMSO]: 2.63 (dd, 1H), 2.76 (dd, 1H),3.39 (s, 3H), 3.75 (m, 1H), 4.75 (d, 1H), 7.28 (d, 2H), 7.57 (d, 2H),8.11 (t, 1H), 8.50 (d, 1H), 8.72 (d, 1H)

Ex. threo-Ibb1083, NMR in [D₆-DMSO]: 2.94 (m, 2H), 3.45 (s, 3H), 3.85(m, 1H), 4.74 (d, 1H), 7.18 (d, 2H), 7.46 (d, 2H), 8.06 (t, 1H), 8.33(d, 1H), 8.61 (d, 1H)

Ex. erythro-Ibb1084, NMR: 2.89 (dd, 1H), 3.10 (dd, 1H), 3.51 (m, 1H),3.70 (s, 3H), 4.51 (d, 1H), 7.00 (m, 2H), 7.29 (m, 3H), 7.42 (t, 1H),8.25 (d, 1H), 8.60 (d, 1H)

Ex. threo-Ibb1084, NMR: 2.94 (d, 2H), 3.64 (s, 3H), 3.65 (q, 1H), 4.14(d, 1H), 7.08 (m, 2H), 7.30 (m, 3H), 7.60 (s, 1H), 8.20 (s, 1H), 8.60(s, 1H)

Ex. erythro-Ibb1085, NMR: 2.31 (s, 3H), 2.87 (dd, 1H), 3.07 (dd, 1H),3.48 (m, 1H), 3.70 (s, 3H), 4.47 (d, 1H), 6.87 (d, 2H), 7.08 (d, 2H),7.44 (m, 1H), 8.23 (d, 1H), 8.60 (d, 1H)

Ex. threo-Ibb1085, NMR: 2.31 (s, 3H), 2.91 (d, 2H), 3.59 (s, 3H), 3.61(q, 1H), 4.12 (d, 1H), 6.95 (d, 2H), 7.10 (d, 2H), 7.62 (t, 1H), 8.18(d, 1H), 8.60 (d, 1H)

Ex. erythro-Ibb1087, NMR: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.67 (m, 1H),3.71 (s, 3H), 4.55 (d, 1H), 7.22 (d, 2H), 7.53 (t, 1H), 8.17 (d, 2H),8.31 (d, 1H), 8.65 (d, 1H)

Ex. threo-Ibb1087, NMR: 2.97 (d, 2H), 3.60 (s, 3H), 3.79 (q, 1H), 4.19(d, 1H), 7.33 (d, 2H), 7.69 (t, 1H), 8.20 (d, 2H), 8.26 (bs, 1H), 8.65(bs, 1H)

Ex. erythro-Ibb1088, NMR: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.47 (m, 1H),3.70 (s, 3H), 3.78 (s, 3H), 4.46 (d, 1H), 6.80 (d, 2H), 6.91 (d, 2H),7.44 (s, 1H), 8.25 (s, 1H), 8.60 (s, 1H)

Ex. threo-Ibb1088, NMR: 2.89 (m, 2H), 3.59 (s, 3H), 3.60 (m, 1H), 3.78(s, 3H), 4.11 (d, 1H), 6.81 (d, 2H), 6.99 (d, 2H), 7.61 (t, 1H), 8.19(d, 1H), 8.60 (d, 1H)

Ex. erythro-Ibb1089, NMR: 2.87 (dd, 1H), 3.05 (dd, 1H), 3.52 (m, 1H),3.71 (s, 3H), 4.50 (d, 1H), 6.77 (m, 2H), 7.02 (m, 1H), 7.49 (m, 1H),8.29 (d, 1H), 8.62 (d, 1H)

Ex. threo-Ibb1089, NMR: 2.92 (d, 2H), 3.61 (s, 3H), 3.65 (q, 1H), 4.13(d, 1H), 6.83 (m, 1H), 6.88 (d, 1H), 6.99 (m. 1H), 7.65 (m, 1H), 8.23(d, 1H), 8.62 (d, 1H)

Ex. threo-Ibb1090, NMR: 2.91 (d, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.14(d, 1H), 6.99 (m, 2H), 7.65 (m, 1H), 8.25 (d, 1H), 8.64 (d, 1H)

Ex. erythro-Ibb1092, NMR: 2.28 (s, 3H), 2.87 (dd, 1H), 3.07 (dd, 1H),3.47 (m, 1H), 3.70 (s, 3H), 4.49 (d, 1H), 6.77 (s, 1H), 6.80 (d, 1H),7.11 (d, 1H), 7.17 (t, 1H), 7.40 (t, 1H), 8.26 (d, 1H), 8.60 (d, 1H)

Ex. threo-Ibb1092, NMR: 2.28 (s, 3H), 2.91 (d, 2H), 3.60 (s, 3H), 3.61(q, 1H), 4.14 (d, 1H), 6.87 (m, 2H), 7.09 (d, 1H), 7.19 (t, 1H), 7.59(t, 1H), 8.21 (d, 1H), 8.61 (d, 1H)

Ex. erythro-Ibb1093, NMR: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.57 (m, 1H),3.71 (s, 3H), 4.51 (d, 1H), 7.32 (m, 2H), 7.44 (t, 1H), 7.50 (t, 1H),7.62 (m, 1H), 8.30 (d, 1H), 8.65 (d, 1H)

Ex. threo-Ibb1093, NMR: 2.93 (d, 2H), 3.61 (s, 3H), 3.70 (q, 1H), 4.16(d, 1H), 7.39 (m, 2H), 7.46 (t, 1H), 7.62 (m, 1H), 7.63 (m, 1H), 8.25(bs, 1H), 8.66 (bs, 1H)

Ex. erythro-Ibb1094, NMR: 2.90 (dd, 1H), 3.09 (dd, 1H), 3.68 (m, 1H),3.70 (s, 3H), 4.53 (d, 1H), 7.42 (m, 1H), 7.55 (m, 2H), 7.89 (t, 1H),8.19 (m, 1H), 8.32 (d, 1H), 8.66 (d, 1H)

Ex. threo-Ibb1094, NMR: 2.98 (d, 2H), 3.61 (s, 3H), 3.80 (q, 1H), 4.21(d, 1H), 7.51 (m, 2H), 7.68 (t, 1H), 8.00 (t, 1H), 8.17 (m, 1H), 8.26(d, 1H), 8.65 (d, 1H)

Ex. Ibb1096 (erythro-Ibb1096: threo-Ibb1096=55:45), NMR:

erythro-Ibb1096: 2.83 (dd, 1H), 3.04 (dd, 1H), 3.68 (s, 3H), 3.97 (q,1H), 4.53 (d, 1H), 7.54 (t, 1H), 8.30 (d, 1H), 8.62 (d, 1H)

threo-Ibb1096: 3.01 (m, 2H), 3.58 (s, 3H), 3.93 (m, 1H), 4.22 (d, 1H),7.77 (t, 1H), 8.30 (d, 1H), 8.60 (d, 1H)

Ex. erythro-Ibb1103, NMR: 2.84 (dd, 1H), 3.03 (dd, 1H), 3.69 (s, 3H),3.98 (m, 1H), 4.54 (d, 1H), 7.14 (m, 3H), 7.59 (t, 1H), 8.33 (d, 1H),8.65 (d, 1H)

Ex. threo-Ibb1103, NMR: 3.00 (m, 2H), 3.59 (s, 3H), 3.97 (m, 1H), 4.20(d, 1H), 6.91 (m, 1H), 7.13 (m, 2H), 7.80 (t, 1H), 8.34 (d, 1H), 8.64(d, 1H)

Ex. erythro-Ibb1104, NMR: 2.81 (dd, 1H), 3.01 (dd, 1H), 3.691 (s, 3H),3.92 (q, 1H), 4.51 (d, 1H), 6.71 (m, 1H), 6.94 (m, 1H), 7.36 (m, 1H),7.58 (t, 1H), 8.32 (d, 1H), 8.64 (d, 1H)

Ex. threo-Ibb1104, NMR: 2.98 (m, 2H), 3.58 (s, 3H), 3.90 (q, 1H), 4.19(d, 1H), 6.82 (m, 2H), 7.10 (m, 1H), 7.78 (t, 1H), 8.32 (d, 1H), 8.62(d, 1H)

Ex. erythro-Ibb1105, NMR: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.71 (s, 3H),3.95 (q, 1H), 4.53 (d, 1H), 6.92 (m, 1H), 6.99 (m, 1H), 7.10 (m, 1H),7.60 (m, 1H), 8.36 (d, 1H), 8.66 (d, 1H)

Ex. erythro-1-Ibb1105, NMR: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.69 (s, 3H),3.94 (q, 1H), 4.53 (d, 1H), 6.92 (m, 1H), 6.99 (m, 1H), 7.10 (m, 1H),7.60 (t, 1H), 8.35 (d, 1H), 8.65 (d, 1H), chiral HPLC: rt=26.9 min,mobile phase d

Ex. erythro-2-Ibb1105, NMR: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.69 (s, 3H),3.94 (q, 1H), 4.53 (d, 1H), 6.92 (m, 1H), 6.99 (m, 1H), 7.10 (m, 1H),7.60 (t, 1H), 8.35 (d, 1H), 8.65 (d, 1H), chiral HPLC: rt=29.2 min,mobile phase d

Ex. threo-Ibb1105, NMR: 2.98 (m, 2H), 3.60 (s, 3H), 3.89 (q, 1H), 4.20(d, 1H), 6.86 (m, 1H), 7.00 (m, 2H), 7.80 (m, 1H), 8.35 (d, 1H), 8.63(d, 1H)

Ex. threo-1-Ibb1105, NMR: 2.98 (m, 2H), 3.60 (s, 3H), 3.90 (q, 1H), 4.20(d, 1H), 6.86 (m, 1H), 7.00 (m, 2H), 7.80 (t, 1H), 8.34 (d, 1H), 8.63(d, 1H), chiral HPLC: rt=10.9 min, mobile phase c

Ex. threo-2-Ibb1105, NMR: 2.98 (m, 2H), 3.60 (s, 3H), 3.90 (q, 1H), 4.20(d, 1H), 6.85 (m, 1H), 7.00 (m, 2H), 7.80 (t, 1H), 8.34 (d, 1H), 8.63(d, 1H), chiral HPLC: rt=15.1 min, mobile phase c

Ex. erythro-Ibb1106, NMR: 2.88 (d, 2H), 3.60 (s, 3H), 4.09 (q, 1H), 4.39(d, 1H), 6.92 (t, 2H), 7.82 (m, 1H), 8.47 (d, 1H), 8.68 (d, 1H)

Ex. erythro-1-Ibb1106, NMR: 2.88 (d, 2H), 3.60 (s, 3H), 4.09 (q, 1H),4.39 (d, 1H), 6.92 (t, 2H), 7.83 (m, 1H), 8.47 (d, 1H), 8.69 (d, 1H);chiral HPLC: rt 8.7 min, mobile phase b

Ex. erythro-2-Ibb1106, NMR: 2.88 (d, 2H), 3.60 (s, 3H), 4.09 (q, 1H),4.39 (d, 1H), 6.92 (t, 2H), 7.83 (m, 1H), 8.47 (d, 1H), 8.69 (d, 1H);chiral HPLC: rt 9.8 min, mobile phase b

Ex. threo-Ibb1106, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.17(m, 2H), 6.79 (t, 2H), 7.78 (m, 1H), 8.18 (d, 1H), 8.55 (d, 1H)

Ex. threo-1-Ibb1106, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H),4.17 (m, 2H), 6.79 (t, 2H), 7.18 (m, 1H), 7.78 (t, 1H), 8.18 (d, 1H),8.55 (d, 1H); chiral HPLC: rt 7.3 min, mobile phase a

Ex. threo-2-Ibb1106, NMR: 3.12 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H),4.17 (m, 2H), 6.79 (t, 2H), 7.18 (m, 1H), 7.78 (t, 1H), 8.18 (d, 1H),8.55 (d, 1H); 7.3 min, chiral HPLC: rt 9.0 min, mobile phase a

Ex. erythro-Ibb1107, NMR: 2.84 (dd, 1H), 3.02 (dd, 1H), 3.50 (m, 1H),3.71 (s, 3H), 4.48 (d, 1H), 6.74 (m, 1H), 6.91 (m, 1H), 7.09 (m, 1H),7.53 (t, 1H), 8.30 (d, 1H), 8.64 (d, 1H)

Ex. threo-Ibb1107, NMR: 2.88 (d, 2H), 3.61 (s, 3H), 3.62 (q, 1H), 4.12(d, 1H), 6.86 (m, 1H), 6.96 (m, 1H), 7.11 (m, 1H), 7.67 (t, 1H), 8.24(d, 1H), 8.64 (d, 1H)

Ex. threo-Ibb1108, NMR: 2.90 (d, 2H), 3.62 (s, 3H), 3.64 (q, 1H), 4.13(d, 1H), 6.67 (m, 2H), 6.75 (m. 1H), 7.70 (m, 1H), 8.27 (d, 1H), 8.65(d, 1H)

Ex. erythro-Ibb1119, NMR: 2.84 (d, 2H), 3.60 (s, 3H), 4.03 (q, 1H), 4.35(d, 1H), 6.98 (m, 2H), 7.85 (t, 1H), 8.48 (d, 1H), 8.70 (d, 1H)

Ex. threo-Ibb1119, NMR: 3.11 (dd, 1H), 3.21 (dd, 1H), 3.64 (s, 3H), 4.14(m, 2H), 6.85 (m, 2H), 7.81 (m, 1H), 8.20 (d, 1H), 8.59 (d, 1H)

Ex. erythro-Ibb1123, NMR: 2.84 (dd, 1H), 3.03 (dd, 1H), 3.57 (q, 1H),3.71 (s, 3H), 4.50 (d, 1H), 7.25 (m, 1H), 7.32 (m, 1H), 7.47 (m, 1H),7.57 (m, 1H), 8.32 (m, 1H), 8.68 (m, 1H)

Ex. threo-Ibb1123, NMR: 2.90 (d, 2H), 3.61 (s, 3H), 3.69 (q, 1H), 4.15(d, 1H), 7.34 (d, 1H), 7.45 (s, 1H), 7.50 (dd, 1H), 7.71 (s, 1H), 8.28(s, 1H), 8.69 (s, 1H)

Ex. Ibb1126 (erythro-Ibb1126: threo-Ibb26=56:44), NMR: erythro-Ibb1126:2.87 (dd, 1H), 3.07 (dd, 1H), 3.47 (m, 1H), 3.71 (s, 3H), 4.52 (d, 1H),6.99 (m, 4H), 7.56 (dd, 1H), 7.86 (m, 1H) threo-Ibb1126: 2.90 (m, 2H),3.61 (s, 3H), 3.64 (q, 1H), 4.15 (d, 1H), 7.04 (m, 4H), 7.72 (dd, 1H),7.80 (m, 1H)

Ex. threo-Ibb1126: 2.90 (m, 2H), 3.61 (s, 3H), 3.64 (q, 1H), 4.15 (d,1H), 7.04 (m, 4H), 7.72 (dd, 1H), 7.80 (m, 1H)

Ex. Ibb1127 (erythro-Ibb1127: threo-Ibb1127=34:66), NMR:

erythro-Ibb1127: 2.86 (dd, 1H), 3.06 (dd, 1H), 3.48 (m, 1H), 3.71 (s,3H), 4.52 (d, 1H), 6.96 (d, 2H), 7.29 (d, 2H), 7.61 (dd, 1H), 7.86 (m,1H)

threo-Ibb1127: 2.89 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.15 (d, 1H),7.02 (d, 2H), 7.30 (d, 2H), 7.75 (dd, 1H), 7.81 (m, 1H)

Ex. erythro-Ibb1127: 2.86 (dd, 1H), 3.06 (dd, 1H), 3.48 (m, 1H), 3.71(s, 3H), 4.52 (d, 1H), 6.96 (d, 2H), 7.29 (d, 2H), 7.61 (dd, 1H), 7.86(m, 1H)

Ex. threo-Ibb1127: 2.89 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.15 (d,1H), 7.02 (d, 2H), 7.30 (d, 2H), 7.75 (dd, 1H), 7.81 (m, 1H)

Ex. Ibb1128 (erythro-Ibb1128: threo-Ibb1128=68:32), NMR:

erythro-Ibb1128: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.46 (m, 1H), 3.71 (s,3H), 4.52 (d, 1H), 6.89 (d, 2H), 7.44 (d, 2H), 7.61 (dd, 1H), 7.86 (m,1H)

threo-Ibb1128: 2.88 (m, 2H), 3.61 (s, 3H), 3.62 (q, 1H), 4.15 (d, 1H),6.96 (d, 2H), 7.46 (d, 2H), 7.75 (dd, 1H), 7.81 (m, 1H)

Ex. erythro-Ibb1128: 2.85 (dd, 1H), 3.06 (dd, 1H), 3.46 (m, 1H), 3.71(s, 3H), 4.52 (d, 1H), 6.89 (d, 2H), 7.44 (d, 2H), 7.61 (dd, 1H), 7.86(m, 1H)

Ex. threo-Ibb1128: 2.88 (m, 2H), 3.61 (s, 3H), 3.62 (q, 1H), 4.15 (d,1H), 6.96 (d, 2H), 7.46 (d, 2H), 7.75 (dd, 1H), 7.81 (m, 1H)

Ex. Ibb1129 (erythro-Ibb1129: threo-Ibb1129=59:41), NMR:

erythro-Ibb1129: 2.90 (dd, 1H), 3.11 (dd, 1H), 3.48 (m, 1H), 3.71 (s,3H), 4.54 (d, 1H), 6.99 (m, 2H), 7.51 (dd, 1H), 7.84 (m, 1H)

threo-Ibb1129: 2.94 (m, 2H), 3.61 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H),7.05 (m, 2H), 7.69 (dd, 1H), 7.78 (m, 1H)

Ex. Ibb1131 (erythro-Ibb1131: threo-Ibb1131=40:60), NMR:

erythro-Ibb1131: 2.89 (dd, 1H), 3.08 (dd, 1H), 3.57 (m, 1H), 3.72 (s,3H), 4.56 (d, 1H), 7.17 (d, 2H), 7.63 (m, 3H), 7.89 (m, 1H)

threo-Ibb1131: 2.91 (m, 2H), 3.61 (s, 3H), 3.71 (q, 1H), 4.20 (d, 1H),7.26 (d, 2H), 7.62 (d, 2H), 7.76 (dd, 1H), 7.85 (m, 1H)

Ex. Ibb1132 (erythro-Ibb1132: threo-Ibb1132=34:66), NMR:

erythro-Ibb1132: 2.90 (dd, 1H), 3.10 (dd, 1H), 3.65 (m, 1H), 3.72 (s,3H), 4.59 (d, 1H), 7.25 (d, 2H), 7.68 (dd, 1H), 7.91 (m, 1H), 8.19 (d,2H)

threo-Ibb1132: 2.97 (m, 2H), 3.61 (s, 3H), 3.78 (q, 1H), 4.23 (d, 1H),7.34 (d, 2H), 7.82 (dd, 1H), 7.86 (m, 1H), 8.21 (d, 2H)

Ex. Ibb1133 (erythro-Ibb1133: threo-Ibb1133=57:43), NMR:

erythro-Ibb1133: 2.86 (dd, 1H), 3.07 (dd, 1H), 3.43 (m, 1H), 3.71 (s,3H), 3.79 (s, 3H), 4.50 (d, 1H), 6.82 (d, 2H), 6.91 (d, 2H), 7.53 (dd,1H), 7.83 (m, 1H)

threo-Ibb1133: 2.89 (m, 2H), 3.58 (q, 1H), 3.61 (s, 3H), 3.78 (s, 3H),4.12 (d, 1H), 6.83 (d, 2H), 6.96 (d, 2H), 7.69 (dd, 1H), 7.76 (m, 1H)

Ex. erythro-Ibb1133: 2.86 (dd, 1H), 3.07 (dd, 1H), 3.43 (m, 1H), 3.71(s, 3H), 3.79 (s, 3H), 4.50 (d, 1H), 6.82 (d, 2H), 6.91 (d, 2H), 7.53(dd, 1H), 7.83 (m, 1H)

Ex. Ibb1134 (erythro-Ibb1134: threo-Ibb1134=54:46), NMR:

erythro-Ibb1134: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72 (s,3H), 4.53 (d, 1H), 7.60 (dd, 1H), 7.89 (d, 1H)

threo-Ibb1134: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.16 (d, 1H),7.76 (dd, 1H), 7.82 (d, 1H)

Ex. erythro-Ibb1134: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72(s, 3H), 4.53 (d, 1H), 7.60 (dd, 1H), 7.89 (d, 1H)

Ex. erythro-1-Ibb1134: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72(s, 3H), 4.53 (d, 1H), 7.60 (dd, 1H), 7.89 (d, 1H)

Ex. erythro-2-Ibb1134: 2.87 (dd, 1H), 3.06 (dd, 1H), 3.50 (m, 1H), 3.72(s, 3H), 4.53 (d, 1H), 7.60 (dd, 1H), 7.89 (d, 1H)

Ex. threo-Ibb1134: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.16 (d,1H), 7.76 (dd, 1H), 7.82 (d, 1H)

Ex. threo-1-Ibb1134: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.16 (d,1H), 7.76 (dd, 1H), 7.82 (d, 1H)

Ex. threo-2-Ibb1134: 2.92 (m, 2H), 3.62 (s, 3H), 3.63 (q, 1H), 4.16 (d,1H), 7.76 (dd, 1H), 7.82 (d, 1H); chiral HPLC: 30.7 min, mobile phase d

Ex. Ibb1139 (erythro-Ibb1139: threo-Ibb1139=37:63), NMR:

erythro-Ibb1139, NMR: 2.90 (dd, 1H), 3.09 (dd, 1H), 3.65 (m, 1H), 3.71(s, 3H), 4.57 (d, 1H), 7.41 (dt, 1H), 7.53 (t, 1H), 7.68 (dd, 1H), 7.93(m, 2H), 8.21 (m, 1H)

threo-Ibb1139, NMR: 2.98 (d, 2H), 3.62 (s, 3H), 3.80 (q, 1H), 4.26 (d,1H), 7.48 (dt, 1H), 7.52 (t, 1H), 7.82 (dd, 1H), 7.88 (m, 1H), 8.02 (m,1H), 8.20 (m, 1H)

Ex. erythro-Ibb1148, NMR: 2.84 (dd, 1H), 3.05 (dd, 1H), 3.70 (s, 3H),3.96 (m, 1H), 4.58 (d, 1H), 7.16 (m, 3H), 7.72 (dd, 1H), 7.92 (m, 1H)

Ex. threo-Ibb1148, NMR: 3.02 (m, 2H), 3.60 (s, 3H), 3.96 (q, 1H), 4.22(d, 1H), 6.90 (m, 1H), 7.06 (m, 1H), 7.13 (m, 1H), 7.93 (m, 2H)

Ex. erythro-Ibb1149, NMR: 2.82 (dd, 1H), 3.04 (dd, 1H), 3.70 (s, 3H),3.90 (q, 1H), 4.55 (d, 1H), 6.71 (m, 1H), 6.96 (m, 1H), 7.38 (m, 1H),7.70 (dd, 1H), 7.91 (m, 1H)

Ex. threo-Ibb1149, NMR: 2.99 (m, 2H), 3.60 (s, 3H), 3.88 (q, 1H), 4.20(d, 1H), 6.82 (m, 2H), 7.10 (m, 1H), 7.91 (m, 2H)

Ex. Ibb1150 (erythro-Ibb1150: threo-Ibb1150=53:47), NMR:

erythro-Ibb1150: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.71 (s, 3H), 3.91 (m,1H), 4.57 (d, 1H), 6.94 (m, 1H), 7.00 (m, 1H), 7.12 (m, 1H), 7.71 (dd,1H), 7.93 (m, 1H)

threo-Ibb1150: 2.99 (m, 2H), 3.61 (s, 3H), 3.89 (q, 1H), 4.22 (d, 1H),6.86 (m, 1H), 7.00 (m, 2H), 7.12 (m, 1H), 7.93 (m, 2H)

Ex. erythro-Ibb1150: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.71 (s, 3H), 3.91(m, 1H), 4.57 (d, 1H), 6.94 (m, 1H), 7.00 (m, 1H), 7.12 (m, 1H), 7.71(dd, 1H), 7.93 (m, 1H)

Ex. Ibb1151 (erythro-Ibb1151: threo-Ibb1151=52:48), NMR:

erythro-Ibb1151: 2.88 (dd, 1H), 2.95 (dd, 1H), 3.62 (s, 3H), 4.16 (m,1H), 4.45 (d, 1H), 6.93 (t, 2H), 7.31 (m, 1H), 7.96 (dd, 1H), 8.07 (m,1H)

threo-Ibb1151: 3.11 (dd, 1H), 3.23 (dd, 1H), 3.63 (s, 3H), 4.07 (q, 1H),4.21 (d, 1H), 6.81 (t, 2H), 7.21 (m, 1H), 7.78 (m, 1H), 7.94 (dd, 1H)

Ex. Ibb1152 (erythro-Ibb1152: threo-Ibb1152=63:37), NMR:

erythro-Ibb1152, NMR: 2.83 (dd, 1H), 3.02 (dd, 1H), 3.47 (m, 1H), 3.72(s, 3H), 4.51 (d, 1H), 6.73 (m, 1H), 6.94 (m, 1H), 7.10 (m, 1H), 7.65(dd, 1H), 7.90 (m, 1H)

threo-Ibb1152, NMR: 2.88 (d, 2H), 3.61 (q, 1H), 3.62 (s, 3H), 4.15 (d,1H), 6.82 (m, 1H), 6.96 (m, 1H), 7.11 (m, 1H), 7.77 (dd, 1H), 7.84 (m,1H)

Ex. erythro-Ibb1152, NMR: 2.83 (dd, 1H), 3.02 (dd, 1H), 3.47 (m, 1H),3.72 (s, 3H), 4.51 (d, 1H), 6.73 (m, 1H), 6.94 (m, 1H), 7.10 (m, 1H),7.65 (dd, 1H), 7.90 (m, 1H)

Ex. erythro-Ibb1164: 2.87 (m, 2H), 3.62 (s, 3H), 4.00 (q, 1H), 4.39 (d,1H), 6.99 (d, 2H), 7.79 (dd, 1H), 8.07 (m, 1H)

Ex. threo-Ibb1164: 3.08 (dd, 1H), 3.22 (dd, 1H), 3.64 (s, 3H), 4.10 (m,1H), 4.18 (d, 1H), 6.87 (d, 2H), 7.80 (m, 1H), 7.95 (dd, 1H)

Ex. erythro-Ibb1622, NMR: 2.28 (s, 3H), 2.83 (dd, 1H), 3.00 (dd, 1H),3.52 (m, 1H), 3.67 (s, 3H), 4.40 (d, 1H), 6.95 (d, 2H), 7.15 (t, 1H),7.24 (d, 2H), 8.19 (bs, 1H), 8.39 (bs, 1H)

Ex. threo-Ibb1622, NMR: 2.33 (s, 3H), 2.89 (d, 2H), 3.58 (s, 3H), 3.64(q, 1H), 4.10 (d, 1H), 7.04 (d, 2H), 7.27 (d, 2H), 7.29 (t, 1H), 8.14(d, 1H), 8.39 (d, 1H)

Ex. erythro-Ibb2162, NMR: 2.87 (dd, 1H), 3.11 (dd, 1H), 3.50 (m, 1H),3.73 (s, 3H), 4.65 (d, 1H), 6.92 (d, 2H), 7.27 (d, 2H), 7.62 (m, 1H),8.55 (d, 1H), 8.82 (d, 1H)

Ex. threo-Ibb2162, NMR: 2.91 (m, 2H), 3.61 (s, 3H), 3.64 (q, 1H), 4.23(d, 1H), 7.01 (d, 2H), 7.30 (d, 2H), 7.76 (m, 1H), 8.48 (d, 1H), 8.82(d, 1H)

Ex. erythro-Ibb2186, NMR: 2.90 (dd, 1H), 3.05 (dd, 1H), 3.66 (s, 3H),4.10 (m, 1H), 4.58 (d, 1H), 6.90 (t, 2H), 7.33 (m, 1H), 7.90 (t, 1H),8.75 (d, 1H), 8.87 (d, 1H)

Ex. threo-Ibb2186, NMR: 3.15 (dd, 1H), 3.24 (dd, 1H), 3.64 (s, 3H), 4.17(m, 1H), 4.27 (d, 1H), 6.80 (t, 2H), 7.21 (m, 1H), 7.85 (t, 1H), 8.50(d, 1H), 8.76 (d, 1H)

Ex. erythro-Ibb3909, NMR: 2.87 (dd, 1H), 3.02 (dd, 1H), 3.57 (m, 1H),3.71 (s, 3H), 4.50 (d, 1H), 7.21 (m, 3H), 7.55 (m, 1H), 8.31 (m, 1H),8.68 (m, 1H)

Ex. threo-Ibb3909, NMR: 2.89 (d, 2H), 3.61 (s, 3H), 3.70 (q, 1H), 4.15(d, 1H), 7.21 (m, 1H), 7.40 (d, 1H), 8.27 (d, 1H), 8.68 (d, 1H)

Ex. erythro-Ibb3783, NMR: 2.84 (dd, 1H), 3.02 (dd, 1H), 3.46 (m, 1H),3.70 (s, 3H), 3.87 (s, 3H), 4.46 (d, 1H), 6.69 (m, 1H), 6.80 (dd, 1H),6.85 (t, 1H), 7.50 (t, 1H), 8.28 (d, 1H), 8.63 (d, 1H)

Ex. threo-Ibb3783, NMR: 2.88 (m, 2H), 3.58 (q, 1H), 3.61 (s, 3H), 3.87(s, 3H), 4.10 (d, 1H), 6.85 (m, 3H), 7.66 (t, 1H), 8.21 (d, 1H), 8.62(d, 1H)

Ex. erythro-Ibb3937, NMR: 2.89 (dd, 1H), 3.09 (dd, 1H), 3.60 (m, 1H),3.71 (s, 3H), 4.53 (d, 1H), 7.15 (d, 2H), 7.47 (m, 1H), 7.56 (d, 2H),8.30 (bs, 1H), 8.64 (bs, 1H)

Ex. threo-Ibb3937, NMR: 2.94 (m, 2H), 3.60 (s, 3H), 3.74 (q, 1H), 4.17(d, 1H), 7.26 (d, 2H), 7.59 (d, 2H), 7.64 (t, 1H), 8.26 (d, 1H), 8.64(d, 1H)

(B) Formulation Examples

-   a) A dust is obtained by mixing 10 parts by weight of a compound of    the formula (I) and 90 parts by weight of talc as inert substance    and comminuting the mixture in a hammer mill.-   b) A wettable powder which is readily dispersible in water is    obtained by mixing 25 parts by weight of a compound of the formula    (I), 64 parts by weight of kaolin-containing quartz as inert    substance, 10 parts by weight of potassium lignosulphonate and 1    part by weight of sodium oleoylmethyltaurate as wetting agent and    dispersant, and grinding the mixture in a pinned-disc mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) with 6    parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3    parts by weight of isotridecanol polyglycol ether (8 EO) and 71    parts by weight of paraffinic mineral oil (boiling range for example    about 255 to above 277° C.) and grinding the mixture in a ball mill    to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I), 75 parts by weight of    cyclohexanone as solvent and 10 parts by weight of oxyethylated    nonylphenol as emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I),        -   10 parts by weight of calcium lignosulphonate,        -   5 parts by weight of sodium laurylsulphate,        -   3 parts by weight of polyvinyl alcohol and        -   7 parts by weight of kaolin,    -   grinding the mixture in a pinned-disc mill, and granulating the        powder in a fluidized bed by spray application of water as a        granulating liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting    -   25 parts by weight of a compound of the formula (I),    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulphonate,    -   2 parts by weight of sodium oleoylmethyltaurinate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water,    -   on a colloid mill, subsequently grinding the mixture in a bead        mill and atomizing and drying the resulting suspension in a        spray tower by means of a single-substance nozzle.

(C) Biological Examples 1. Herbicidal Pre-Emergence Action

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantswere placed in wood-fibre pots in sandy loam and covered with soil. Thecompounds (I) according to the invention, formulated in the form ofwettable powders (WP), were then applied as aqueous suspension oremulsion at a water application rate of 600 I/ha (converted) with theaddition of 0.2% of wetting agent to the surface of the covering soil.

After the treatment, the pots were placed in a greenhouse and kept undergood growth conditions for the test plants. After about 3 weeks, theeffect of the preparations was scored visually in comparison withuntreated controls as percentages. For example, 100% activity=the plantshave died, 50% herbicidal activity or damage=the plants have beenreduced by 50% or the plant mass has been reduced by 50%, 0%activity=like control plants.

Compounds (I) according to the invention, for example the compounds Nos.erythro-Ibb2, threo-Ibb2, erythro-Ibb9, threo-Ibb9, threo-Ibb10,erythro-Ibb25, threo-Ibb25, erythro-Ibb26, threo-Ibb26, erythro-Ibb542,threo-Ibb542, erythro-Ibb565, threo-Ibb565, erythro-Ibb566,threo-Ibb566, erythro-Ibb1081, threo-Ibb1081, Ibb1082, erythro-Ibb1082,erythro-1-Ibb1082, erythro-2-Ibb1082, threo-Ibb1082, threo-1-Ibb1082,threo-2-Ibb1082, erythro-Ibb1084, threo-Ibb1084, erythro-Ibb1085,threo-Ibb1085, erythro-Ibb1088, threo-Ibb1088, erythro-Ibb1089,threo-Ibb1089, threo-Ibb1090, erythro-Ibb1092, erythro-Ibb1093,threo-Ibb1093, erythro-Ibb1094, threo-Ibb1094, Ibb1096, erythro-Ibb1096,threo-Ibb1096, erythro-Ibb1103, threo-Ibb1103, erythro-Ibb1104,threo-Ibb1104, erythro-Ibb1105, erythro-1-Ibb1105, erythro-2-Ibb1105,threo-Ibb1105, threo-1-Ibb1105, threo-2-Ibb1105, erythro-Ibb1106,erythro-1-Ibb1106, erythro-2-Ibb1106, threo-Ibb1106, threo-1-Ibb1106,threo-2-Ibb1106, erythro-Ibb1107, threo-Ibb1107, threo-Ibb1108,erythro-Ibb1622, threo-Ibb1622, erythro-Ibb3783, threo-Ibb3783 from theabove Tables 2 to 2f have good herbicidal activity (70% to 100%activity) against a plurality of harmful plants at an application rateof 320 g or less of active substance per hectare when applied by thepre-emergence method.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2,threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26,threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1084, threo-Ibb1084,erythro-Ibb1088, threo-Ibb1088, threo-Ibb1089, threo-Ibb1090,threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 havevery good activity (90-100%) against harmful plants such as Echinochloacrus-galli when applied by the pre-emergence method at an applicationrate of 0.32 kg of active substance per hectare.

For example, the compounds Nos. erythro-Ibb2, threo-Ibb2, erythro-Ibb9,threo-Ibb10, erythro-Ibb26, Ibb1082, threo-Ibb1082, threo-Ibb1084,threo-Ibb1088, threo-Ibb1089, threo-Ibb1090, threo-Ibb1105,erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 have very good activity(90-100%) against harmful plants such as Setaria virides when applied bythe pre-emergence method at an application rate of 0.32 kg of activesubstance per hectare.

For example, the compounds Nos. erythro-Ibb26, threo-Ibb26,threo-Ibb1089, erythro-Ibb1105, erythro-Ibb1106 and threo-Ibb1106 havevery good activity (80-100%) against harmful plants such as Polygonumconvolvulus when applied by the pre-emergence method at an applicationrate of 0.32 kg of active substance per hectare. For example, thecompounds Nos. erythro-Ibb9, threo-Ibb9, Ibb1082, threo-Ibb1082,erythro-Ibb1088, threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089,threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106,threo-Ibb1106 and threo-Ibb1108 have very good activity (90-100%)against harmful plants such as Veronica persica when applied by thepre-emergence method at an application rate of 0.32 kg of activesubstance per hectare.

For example, the compounds Nos. erythro-Ibb9, threo-Ibb9, erythro-Ibb26,threo-Ibb26, Ibb1082, threo-Ibb1082, threo-Ibb1084, threo-Ibb1088,erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106 and threo-Ibb1106 havevery good activity (90-100%) against harmful plants such as Violatricolor when applied by the pre-emergence method at an application rateof 0.32 kg of active substance per hectare.

For example, the compounds Nos. erythro-Ibb2, threo-Ibb2, erythro-Ibb9,threo-Ibb9, threo-Ibb10, erythro-Ibb26, threo-Ibb26, Ibb1082,threo-Ibb1082, erythro-Ibb1088, threo-Ibb1088, threo-Ibb1090,erythro-Ibb1106 and threo-Ibb1106 have very good activity (80-100%)against harmful plants such as Alopecurus myosuroides when applied bythe pre-emergence method at an application rate of 0.32 kg of activesubstance per hectare.

For example, the compounds Nos. erythro-Ibb2, threo-Ibb10,erythro-Ibb26, threo-Ibb26, threo-Ibb1082, erythro-Ibb1105,threo-Ibb1105, erythro-Ibb1106 and threo-Ibb1106 have very good activity(80-100%) against harmful plants such as Amaranthus retroflexus whenapplied by the pre-emergence method at an application rate of 0.32 kg ofactive substance per hectare.

2. Herbicidal Post-Emergence Action

Seeds of monocotyledonous and dicotyledonous weeds and crop plants wereplaced in sandy loam in wood-fibre pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants were treated at the one-leaf stage, wherethe compounds (I) according to the invention, formulated in the form ofwettable powders (WP), were applied by spraying as aqueous suspension oremulsion at a water application rate of 600 I/ha (converted) with theaddition of 0.2% of wetting agent to the green parts of the plants.After the test plants had been kept in the greenhouse under optimumgrowth conditions for about 3 weeks, the activity of the preparationswas rated visually in comparison to untreated controls in percent (%).For example, 100% activity=the plants have died, 50% herbicidal activityor damage=the plants have been reduced by 50% or the plant mass has beenreduced by 50%, 0% activity=like control plants.

As shown by the results, compounds (I) according to the invention, forexample the compounds Nos. erythro-Ibb2, threo-Ibb2, erythro-Ibb9,threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26,threo-Ibb26, erythro-Ibb542, threo-Ibb542, erythro-Ibb565, threo-Ibb565,erythro-Ibb566, threo-Ibb566, erythro-Ibb1081, threo-Ibb1081, Ibb1082,erythro-Ibb1082, erythro-1-Ibb1082, erythro-2-Ibb1082, threo-Ibb1082,threo-1-Ibb1082, threo-2-Ibb1082, erythro-Ibb1084, threo-Ibb1084,erythro-Ibb1085, threo-Ibb1085, erythro-Ibb1088, threo-Ibb1088,erythro-Ibb1089, threo-Ibb1089, threo-Ibb1090, erythro-Ibb1092,erythro-Ibb1093, threo-Ibb1093, erythro-Ibb1094, threo-Ibb1094, Ibb1096,erythro-Ibb1096, threo-Ibb1096, erythro-Ibb1103, threo-Ibb1103,erythro-Ibb1104, threo-Ibb1104, erythro-Ibb1105, erythro-1-Ibb1105,erythro-2-Ibb1105, threo-Ibb1105, threo-1-Ibb1105, threo-2-Ibb1105,erythro-Ibb1106, erythro-1-Ibb1106, erythro-2-Ibb1106, threo-Ibb1106,threo-1-Ibb1106, threo-2-Ibb1106, erythro-Ibb1107, threo-Ibb1107,threo-Ibb1108, erythro-Ibb1622, threo-Ibb1622, erythro-Ibb3783,threo-Ibb3783 from the above Tables 2 to 2f have good herbicidalactivity (70% to 100% activity) against a plurality of harmful plants atan application rate of 320 g or less of active substance per hectarewhen applied by the post-emergence method.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2,threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26,threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1084, threo-Ibb1084,erythro-Ibb1088, threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089,threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106,threo-Ibb1106 and threo-Ibb1108 have very good activity (80-100%)against harmful plants such as Echinochloa crus-galli when applied bythe post-emergence method at an application rate of 0.32 kg of activesubstance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2,threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26,threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1084, threo-Ibb1084,threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089, threo-Ibb1090,erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 andthreo-Ibb1108 also have very good activity (80-100%) against harmfulplants such as Setaria virides when applied by the post-emergence methodat an application rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2,erythro-Ibb9, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25,erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, erythro-Ibb1084,threo-Ibb1088, erythro-Ibb1089, threo-Ibb1089, threo-Ibb1090,erythro-Ibb1105, threo-Ibb1105, threo-Ibb1106 and threo-Ibb1108 alsohave very good activity (80-100%) against harmful plants such asVeronica persica when applied by the post-emergence method at anapplication rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2,erythro-Ibb9, threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25,erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082, threo-Ibb1084,erythro-Ibb1088, threo-Ibb1088, threo-Ibb1090, erythro-Ibb1105,threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 and threo-Ibb1108 alsohave very good activity (80-100%) against harmful plants such as Avenafatua when applied by the post-emergence method at an application rateof 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2,threo-Ibb9, threo-Ibb10, erythro-Ibb25, threo-Ibb25, erythro-Ibb26,threo-Ibb26, Ibb1082, threo-Ibb1082, threo-Ibb1084, threo-Ibb1088,threo-Ibb1090 and threo-Ibb1105 also have very good activity (80-100%)against harmful plants such as Alopecurus myosuroides when applied bythe post-emergence method at an application rate of 0.32 kg of activesubstance per hectare.

Here, for example, the compounds Nos. threo-Ibb10, erythro-Ibb25,threo-Ibb25, erythro-Ibb26, threo-Ibb26, threo-Ibb1082, threo-Ibb1084,erythro-Ibb1105, threo-Ibb1105 and threo-Ibb1108 also have very goodactivity (80-100%) against harmful plants such as Cyprus esculentus whenapplied by the post-emergence method at an application rate of 0.32 kgof active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb26 andthreo-Ibb1082 also have very good activity (80-100%) against harmfulplants such as Lolium multiflorum when applied by the post-emergencemethod at an application rate of 0.32 kg of active substance perhectare.

Here, for example, the compounds Nos. erythro-Ibb9 and threo-Ibb26 alsohave very good activity (80-100%) against harmful plants such asStellaria media when applied by the post-emergence method at anapplication rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2,threo-Ibb9, threo-Ibb25, erythro-Ibb26, threo-Ibb26, threo-Ibb1082,threo-Ibb1084, erythro-Ibb1088, threo-Ibb1088, threo-Ibb1090,erythro-Ibb1105, threo-Ibb1105, erythro-Ibb1106, threo-Ibb1106 andthreo-Ibb1108 also have very good activity (80-100%) against harmfulplants such as Abutilon theophrasti when applied by the post-emergencemethod at an application rate of 0.32 kg of active substance perhectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2,threo-Ibb9, erythro-Ibb25, threo-Ibb25, erythro-Ibb26, Ibb1082,threo-Ibb1082, threo-Ibb1084 and erythro-Ibb1105 also have very goodactivity (80-100%) against harmful plants such as Amaranthus retroflexuswhen applied by the post-emergence method at an application rate of 0.32kg of active substance per hectare.

Here, for example, the compounds Nos. threo-Ibb10, erythro-Ibb25,threo-Ibb25, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1082,erythro-Ibb1084, threo-Ibb1084, erythro-Ibb1088, threo-Ibb1088,threo-Ibb1090, erythro-Ibb1105, threo-Ibb1105 and threo-Ibb1108 alsohave very good activity (80-100%) against harmful plants such asPolygonum convolvulus when applied by the post-emergence method at anapplication rate of 0.32 kg of active substance per hectare.

Here, for example, the compounds Nos. erythro-Ibb2, threo-Ibb2,threo-Ibb9, erythro-Ibb26, threo-Ibb26, Ibb1082, threo-Ibb1090 andthreo-Ibb1105 also have very good activity (80-100%) against harmfulplants such as Viola tricolor virides when applied by the post-emergencemethod at an application rate of 0.32 kg of active substance perhectare.

Here, for example, the compounds Nos. erythro-Ibb2, erythro-Ibb26,threo-Ibb26, Ibb1082, threo-Ibb1084, threo-Ibb1088, threo-Ibb1090,threo-Ibb1105 and threo-Ibb1106 also have very good activity (80-100%)against harmful plants such as Pharbitis purpurea when applied by thepost-emergence method at an application rate of 0.32 kg of activesubstance per hectare.

The invention claimed is:
 1. A compound of formula (I) and/or a saltthereof

in which (R¹)_(m) represents m substituents R¹, where R¹, if m=1, oreach of the substituents R¹, if m is greater than 1, independently ofthe others represents halogen, cyano, (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy,(C₂-C₆)-haloalkenyl, or (C₂-C₆)-haloalkynyl, (R²)_(n) represents nsubstituents R², where R², if n=1, or each of the substituents R², if nis greater than 1, independently of the others represents halogen,cyano, nitro, (C₁-C₈)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₁-C₈)-alkoxy, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy, or a radical ofthe formula C(O)OR¹⁰, R³ represents halogen, cyano, nitro,(C₁-C₈)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy,(C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy, or a radical of the formulaC(O)OR¹⁵, R⁴ represents hydrogen or a hydrolyzable optionallysubstituted hydrocarbon radical or optionally substituted heterocyclylradical, where each of the two last-mentioned carbon-containing radicalsincluding substituents has 1 to 30 carbon atoms, or represents ahydrolyzable radical of the formula SiR^(a)R^(b)R^(c), —NR^(a)R^(b) or—N═CR^(c)R^(d), where in the 3 last-mentioned formulae each of theradicals R^(a), R^(b), R^(c) and R^(d) independently of the othersrepresents hydrogen or an optionally substituted hydrocarbon radical,where, however, SiR^(a)R^(b)R^(c) is not SiH₃, where each of theradicals R^(a), R^(b), R^(c) and R^(d) including substituents has up to30 carbon atoms, or represents a hydrolyzable radical of the formula—C(═O)—R^(e) or —P(═O)(R^(f))₂, where R^(e) and the radicals R^(f)independently of one another each represent hydrogen, OH, (C₁-C₈)-alkyl,(C₁-C₄)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₈)-alkyl, (C₁-C₄)-haloalkoxy,(C₁-C₄)-haloalkoxy-(C₁-C₈)-alkyl, (C₃-C₈)-alkenyloxy,(C₃-C₈)-alkenyloxy-(C₁-C₈)-alkyl, (C₃-C₈)-alkynyloxy,(C₃-C₈)-alkynyloxy-(C₁-C₈)-alkyl, —NR*R**, tri-[(C₁-C₄)-alkyl]silyl,tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₈)alkyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkenyl,(C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkynyl,(C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkyl, phenyl, phenyl-(C₁-C₈)-alkyl,phenoxy, phenoxy-(C₁-C₈)-alkyl, phenylamino, orphenylamino-(C₁-C₈)-alkyl, R¹⁰ and R¹⁵ independently of one another eachrepresent hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or a group M, R* and R**independently each represent H, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl,(C₂-C₈)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,[(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,[(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, or phenyl-(C₁-C₄)-alkyl, whereeach of the 4 last-mentioned radicals is optionally substituted in thecycle by one or more identical or different radicals from the groupconsisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxyand (C₁-C₄)-haloalkoxy or, in the case of saturated or partiallyunsaturated cyclic base groups, also oxo, or R* and R** together withthe nitrogen atom represent a 3- to 8-membered heterocycle which, inaddition to the nitrogen atom, may contain one or two further ringheteroatoms from the group consisting of N, O and S and which may beunsubstituted or substituted by one or more radicals from the groupconsisting of (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, M represents anequivalent of a cation that is a metal ion, an ammonium ion which isoptionally substituted by 1 to 4 identical or different radicals fromthe group consisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl, phenyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl,phenyl-(C₁-C₄)-alkyl, or a tertiary sulphonium ion which is optionallysubstituted by 3 identical or different radicals from the groupconsisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl, phenyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl,phenyl-(C₁-C₄)-alkyl, optionally (C₁-C₄)-alkyl, m represents 0, 1, 2 or3, and n represents 0, 1, 2, 3, 4 or
 5. 2. A compound and/or saltthereof according to claim 1, wherein R⁴ represents hydrogen or ahydrolyzable optionally substituted hydrocarbon radical or an optionallysubstituted heterocyclyl radical, where each of the two last-mentionedcarbon-containing radicals including substituents has 1 to 30 carbonatoms, or represents a hydrolyzable radical of the formulaSiR^(a)R^(b)R^(c), —NR^(a)R^(b) or —N═CR^(c)R^(d), where in the 3last-mentioned formulae each of the radicals R^(a), R^(b), R^(c) andR^(d) independently of the others represents hydrogen or an optionallysubstituted hydrocarbon radical, where, however, SiR^(a)R^(b)R^(c) isnot SiH₃, where each of the radicals R^(a), R^(b), R^(c) and R^(d)including substituents has up to 30 carbon atoms, or represents ahydrolyzable radical of the formula —C(═O)—R^(e) or —P(═O)(R^(f))₂,where R^(e) and the radicals R^(f) independently of one another eachrepresent hydrogen, OH, (C₁-C₈)-alkyl, (C₁-C₄-haloalkyl,(C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₈)-alkyl, (C₁-C₄)-haloalkoxy,(C₁-C₄)-haloalkoxy-(C₁-C₈)-alkyl, (C₃-C₈)-alkenyloxy,(C₃-C₈)-alkenyloxy-(C₁-C₈)-alkyl, (C₃-C₈)-alkynyloxy,(C₃-C₈)-alkynyloxy-(C₁-C₈)-alkyl, —NR*R**, tri-[(C₁-C₄)-alkyl]silyl,tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₈)alkyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkenyl,(C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkynyl,(C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkyl, phenyl, phenyl-(C₁-C₈)-alkyl,phenoxy, phenoxy-(C₁-C₈)-alkyl, phenylamino, orphenylamino-(C₁-C₈)-alkyl, and R* and R** independently each representH, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,[(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,[(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, phenyl-(C₁-C₄)-alkyl, whereeach of the 4 last-mentioned radicals is optionally substituted in thecycle by one or more identical or different radicals from the groupconsisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxyand (C₁-C₄)-haloalkoxy or, in the case of saturated or partiallyunsaturated cyclic base groups, also oxo, or R* and R** together withthe nitrogen atom represent a 3- to 8-membered heterocycle which, inaddition to the nitrogen atom, may contain one or two further ringheteroatoms from the group consisting of N, O and S and which may beunsubstituted or substituted by one or more radicals from the groupconsisting of (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo.
 3. A compoundand/or salt thereof according to claim 1, wherein (R¹)_(m) represents msubstituents R¹, where R¹, if m=1, or each of the substituents R¹, if mis greater than 1, independently of the others represents halogen,cyano, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy,(C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₂-C₄)-haloalkenyl, or(C₂-C₄)-haloalkynyl, M represents an equivalent of a cation and mrepresents 0, 1, 2 or
 3. 4. A compound and/or salt thereof according toclaim 1, wherein (R²)_(n) represents n substituents R², where R², ifn=1, or each of the substituents R², if n is greater than 1,independently of the others represents halogen, cyano, nitro,(C₁-C₆)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy,(C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₂-C₄)-haloalkenyl,(C₂-C₄)-haloalkynyl, or a radical of the formula C(O)OR¹⁰, R¹⁰represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or a group M, M represents anequivalent of a cation and n represents 0, 1, 2, 3, 4 or
 5. 5. compoundand/or salt thereof according to claim 1, wherein R³ represents halogen,cyano, nitro, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,(C₁-C₆)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, or a radical ofthe formula C(O)OR¹⁵, R¹⁵ represents hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or a group M, andM represents an equivalent of a cation.
 6. A compound and/or saltthereof according to claim 1, wherein (R¹)_(m) represents m substituentsR¹, where R1, if m=1, or each of the substituents R¹, if m is greaterthan 1, independently of the others represents halogen, cyano,(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, ora radical of the formula C(O)OR⁵, R⁵ represents hydrogen, (C₁-C₄)-alkylor a group M, m represents 0, 1, 2 or 3, (R²)_(n) represents nsubstituents R², where R², if n=1, or each of the substituents R², if nis greater than 1, independently of one another represent halogen,cyano, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy, or a radical of the formula C(O)OR¹⁰, R¹⁰ representshydrogen, (C₁-C₄)-alkyl or a group M, n represents 0, 1, 2, 3, 4 or 5,R³ represents halogen, cyano, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, or a radical of the formulaC(O)OR¹⁵, R¹⁵ represents hydrogen, (C₁-C₄)-alkyl or a group M, and Mrepresents an equivalent of a cation.
 7. A process for preparing acompound of formula (I) and/or a salt thereof as defined in claim 1comprising obtaining a diastereomer mixture of the compound and/or saltof formula (I) comprising the compound (I) to be prepared wherein (a) inthe case of preparation of a diastereomer mixture of the compound and/orsalt of formula (I), reacting a compound of formula (II)

with a compound of formula (III) and/or salt thereof

to give a compound of the formula (I)

where R¹, R², R³, R⁴, m and n in the compounds (II) and (III) are asdefined in the respective compound of the formula (I) to be prepared,and/or (b) reacting a compound of the formula (I*)

in which R is a radical from the group consisting of the radicalspossible for R⁴′ but different from the radical R⁴ in the compound (I)to be prepared, with a compound of formula R⁴—OH in which R⁴ is definedas in formula (I), to give compound (I) and/or salt thereof, where R¹,R², R³, m and n in the compound (I*) are as defined in the compound ofthe formula (I) to be prepared in each case and/or (c) reacting acompound of formula (I*) in which R represents a hydrogen atom with acompound of formula R⁴—OH in which R⁴ is as defined in formula (I), togive a compound of the formula (I) and/or salt thereof, or (d) in thecase in which an optically active compound of a diastereomeric form ofthe compound of the formula (I) and/or salt is prepared, subjecting theracemic mixture of the diastereomeric form of the compound of theformula (I) and/or salt to an optical resolution and isolating thedesired enantiomer in a stereochemical purity of from 60 to 100%,optionally from 70 to 100%, or optionally from 80 to 100%, in particularor optionally from 90 to 100%, based on the mixture of erythro or threoenantiomers present.
 8. A herbicidal and/or plant growth-regulatingcomposition, comprising one or more compounds of formula (I) and/or saltthereof as defined in claim 1 and one or more formulation auxiliariescustomary in crop protection.
 9. A method for controlling harmful plantsand/or for regulating growth of a plant, comprising applying aneffective amount of one or more compounds of formula (I) and/or saltthereof as defined in claim 1 is applied onto a plant, plant seed, soilin which and/or on which a plant grows and/or an area under cultivation.10. A method according to claim 9, that wherein the compound of formula(I) and/or salt thereof is employed for selective control of a harmfulplant and/or for regulating growth in a crop of a useful plant and/orornamental plant.
 11. A compound of formula (I) and/or salt thereofaccording to claim 1 capable of being used as a herbicide and/or plantgrowth regulator.
 12. A herbicide and/or plant growth regulatorcomprising a compound of formula I and/or salt thereof as claimed inclaim 1.